OODAcast - SoundSage

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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

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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

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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

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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/

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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

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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.

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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

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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

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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

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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.

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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 Computing
Quantum Security
Artificial Intelligence
Microelectronics and Friendshoring/Reshoring
The March 2023 National Strategy for Cybersecurity
Governance in the age of ubiquitous computing
What corporate boards should know about technology and cybersecurity governance

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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 “No Way Out” which is dedicated to examining and advancing the use of the theories of John Boyd to help both individuals and businesses seeking to improve their capacity for free and independent action.

Mark is also a continuous learner. He has examined the works of John Boyd from as many perspectives as possible including visiting the archives of his books and papers at the Marine Corps University library at Quantico.

In this OODAcast we ask Mark for his perspectives on Boyd and OODA, resulting in some unique and at times surprising insights. We cover:

Ludwig von Mises and Austrian Economics, the economic theories that many of us (myself included) believe to be the only economic theories grounded on reality. Mises cites the ancient philosopher Heraclitus: Everything is in a ceaseless flux, there is no permanent being; all is change and becoming.Doesn’t that sound like Boyd?
The connection between Boyd’s approaches and realities of physics and biology
How history impacted Boyd’s views on decision-making in competitive environments
How leaders can continue to sharpen the saw and keep learning.
Why treating the OODA Loop as the only concept from Boyd is just wrong. Study of Boyd may start with the OODA loop because it is the most famous of his concepts but it it one of many contributions. This scope of his work is so far beyond that.
Regarding OODA, we discuss the critical aspect of the Orientation step. Mark considers Orientation as our internal operating system that needs to be constantly upgraded and updated to stay relevant for success.

Resources:

Mark McGrath on LinkedIn

The No Way Out podcast

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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 pioneered work on WebRTC proxies that she continued as a fellow at the Open Tech Fund and was eventually released as a Tor-enabling tool called Snowflake.

Serene took a hiatus from working as a full-time engineer to pursue a career as a concert pianist where she quickly gained recognition for her incredible talent. She became one of the few self-taught concert pianists to perform Rachmaninoff’s Piano Concerto No. 3 (which I highly recommend checking out on YouTube). Serene is also known for the audiovisual artistry of her shows which is drawn from her own experiences with synesthesia that results in her seeing music as colors.

As the conflict in Ukraine started, Snowflake started to see exponential usage patterns as Russian citizens looked to circumvent state censorship and Serene decided to build a company around the technology to enhance development and build independent deployment models. That company is called Snowstorm.

With Snowstorm, Serene is focused on saving cyberspace from balkanization and censorship and ensuring that all global citizens have unfiltered access to the Internet. In this OODAcast, we explore Serene's career and then dive into ways we can preserve the original intent of the Internet with censorship resistant and privacy enhancing technology stacks that can be easily deployed and scaled.

Official Bio: SERENE is a concert pianist from a most unexpected trajectory. Though she never attended conservatory, her solo performances have been described by The Paris Review as a “spectacle to match the New York Philharmonic”, and today Serene has become one of the most talked about young talents in classical music, and beyond.

Beyond concertizing, Serene enjoys other collaborations such as her role as composer for Kanye West’s Opera, premiered at Lincoln Center & Art Basel, as well as pianist & technologist with Blue Man Group’s founder, bringing futuristic innovations at the intersection of music and technology while also highlighting her own audiovisual synesthesia.

Previously, Serene was a computer scientist, Google Engineer, and senior research fellow on various projects, before leaving to fully focus on the piano. In the brief years since, she has cultivated a disciplined, personal, and spiritual approach to her music. With her intersections of many disciplines, plus the “ability to enthrall audiences”, she has grown an international following.

Serene is one of very few self-taught pianists who’ve performed Rachmaninoff’s Piano Concerto No. 3, which was described as “unprecedented” —Liszt Academy. Serene loves sharing the beauty and power of classical music with all audiences, everywhere, in all venues ranging from the Vienna Musikverein, to a full orchestra in Golden Gate Park, to a decommissioned Boeing 747.

Additional Links:

Official Website
Snowstorm
Serene on Instagram
Serene Rachmaninoff Concerto

Book Recommendations:

A Thousand Years of Non-linear History
The Making of the Atomic Bomb
The Metamorphosis of Prime Intellect: a novel of the singularity
Accelerando

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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 testified before the U.S. Senate Energy and Natural Resources Committee on energy infrastructure cybersecurity issues and before FERC on the maturity of smart grid cybersecurity standards. He has had recurring conversations on grid security matters with the Senate Select Committee on Intelligence and the National Security Council.

In this OODAcast we discuss Andy’s most recent book, Countering Cyber Sabotage: Introducing Consequence-based Cyber-Informed Engineering. This book introduces INL’s new approach for defending against top-tier cyber adversaries.

Watch as we learn how a hockey player transformed into a cybersecurity champion and author of one of the most important books for engineering for critical infrastructure defense.

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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 professor, responsible for launching the modern American industrial management movement, served as a General in World War II where he solved critical supply chain and logistics issues while also inventing things like sunscreen, and then formed the first venture capital firm that operated with much success and launched the modern VC market.

In addition to discussing Doriot, we delve into lessons learned from his experiences and then a general discussion on innovative and disruptive technologies like AI, issues like privacy, and insights from Spencer's career in journalism, at Meta Foresight, and as a consultant.

Official Bio:

Spencer Ante was recently Head of Insights within the Global Business Marketing group of Meta, where he led the editorial team for the thought leadership platform Meta Foresight. Previous to that he was Managing Director of FTI Consulting, heading up the content and creative team within the Digital and Insights practice of its Strategic Communications segment.

Mr. Ante is an editorial leader and communications marketing executive who specializes in driving integrated, omni-channel content programs and multi-disciplinary teams for top corporations that enhance corporation reputation and drive business results. He brings 15 years of newsroom management experience from leading media outlets to the field of communications and marketing, as well as deep expertise in video, digital, social, and mobile media.

Prior to his consulting work, Mr. Ante was an award-winning journalist who most recently worked at The Wall Street Journal as a Senior Special Writer on its technology team, and as a Deputy Bureau Chief for the Journal’s largest bureau responsible for global business coverage. In 2012, he was part of a team of journalists nominated for the Pulitzer Prize in explanatory reporting for a series on privacy in the digital age. He is the author of Creative Capital: Georges Doriot and the Birth of Venture Capital.

Additional Links:

Creative Capital Book

Spencer on Twitter

Recommended Books:

Shoe Dog

Chip Wars

The Every

Creative Capital: Georges Doriot and the Birth of Venture Capital

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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. His many articles published in major business journals and impactful books on the topic make this case well.

Bob has worked with, studied, and been on corporate boards for years and now teaches corporate governance as an Adjunct Professor of Management at the USC Marshall School of Business. He is co-author of the book The Great Reboot. We examine the book and Bob's approach to helping corporate directors mitigate cyber risk in this OODAcast.

Topics covered include:

How the 1200 strong members of the Digital Directors Network collaborate together to seek to reduce systemic risk.

The creation of the Qualified Technical Expert (QTE) program and how the need for QTEs on boards is analogous to the need to have a Qualified Financial Expert (QFE) on boards when Sarbanes-Oxley drove that requirement.

The new SEC regulations on cybersecurity that will require corporate boards to designate cybersecurity experts.

How the new US Cybersecurity Strategy is helping create positive momentum in corporate America (Bob says "the White House has declared war on systemic risk with this strategy").

Actions directors can take to ensure corporate management is appropriately engaging to mitigate not just cyber attacks against the company, but broader systemic risks. Bob explains that "It's not just enough for board members to ask questions on cyber risk, as the questions are meaningless if corporate directors don't understand the answers." Very well put! Board members should continuously seek to improve their ability to understand. And then on top of that should ask the right questions. What is Bob's view of a powerful question boards should be asking? " What's the value of what we are trying to protect, and how safe is it for what we're spending?"

Bob provides information on an event that brings together the Digital Directors Network called Domino (16-17 May 2023 in Chicago). This is a gathering of 200 of DDN's corporate director, CIO and CISO members for a unique executive learning experience. This year's event will feature keynotes from experts like SEC Commissioner Jaime Lizarraga explaining the new cyber rules being rolled out by the SEC.

For more see:

The Great Reboot

The Digital Directors Network

Bob Zukis on LinkedIn

DDN Domino 16-17 May 2023

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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 career and experiences (which range from startups to nearly a decade at Microsoft, as well as the Blackhat review board, as well as being an Affiliate Professor at University of Washington). We then dive deep into Adam’s most recent book, Threats: What Every Engineer Should Learn from Star Wars

Just what does Star Wars have to do with security engineering? Turns out the movies are full of analogies that can really underscore the importance of good design and operational security.

The very beginning of A New Hope shows a space fight where the empire is seeking to recover data from a breach. The carrier of that breached data, R2-D2, makes it to the planet below. But somehow knows not to show a special recording to Luke, only to Obi-Wan. That is some high end identity management and authorization there.

From this lens Star Wars is not just a space western, it is a cyber espionage thriller. Adam uses the many analogies from Star Wars to make good engineering concepts more memorable and in doing so is doing us all a service.

For more see:

Adam Shostack on LinkedIn

Threats: What Every Engineer Should Learn from Star Wars

Threat Modeling: Designing for Security

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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 of 2022.

In this conversation, we discuss the differences between different investment companies like venture capital, private equity, and hedge funds and discuss the financial and geopolitical mechanics and decision-making approaches that allow for success in each variation.

Official Bio:

Sebastian Mallaby is the Paul A. Volcker senior fellow for international economics at the Council on Foreign Relations (CFR). An experienced journalist and public speaker, Mallaby contributes to a variety of publications, including Foreign Affairs, the Atlantic, the Washington Post, and the Financial Times, where he spent two years as a contributing editor. He is the author of five books, most recently The Power Law: Venture Capital and the Making of the New Future. (Long Bio)

Sebastian’s Books: The Power Law: Venture Capital and the Making of the New Future

More Money Than God: Hedge Funds and the Making of a New Elite

The Man Who Knew: The Life and Times of Alan Greenspan

Sebastian on Twitter

Book Recommendation:The Creativity Code

The Man Who Knew: The Life and Times of Alan Greenspan

The Power Law: Venture Capital and the Art of Disruption

More Money Than God: Hedge Funds and the Making of a New Elite (Council on Foreign Relations Books (Penguin Press))

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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 and in DoD Combatant Commands, and would later serve as the Chairman of the famed National Intelligence Council (NIC). Also served as a senior leader at ODNI, including leading the entire intelligence community as the Principal Deputy Director of National Intelligence from May 13, 2020 until February 2021.

In this OODAcast we learn some of what made Neil tick, diving into his education, his early career intent, the role of serendipity in helping him transition to the intelligence community, and his approach to leadership and management. We also dive into big issues of optimizing intelligence including ways organizations can help guard against cognitive bias.

Neil provides insights into his approaches to: – Training analytical methods and understanding which methods should be applied to which situations – Ways to teach analysts to spot their own cognitive bias and seek to mitigate, and ways to use the benefits of teams to help spot and mitigate analytical flaws – Ways to avoid deception by adversaries – Methods that can improve mental models – The mission of the National Intelligence Council and its key products, including those available to the public – Ways to find balance between the need to serve policy makers and military leaders without being captured by and influenced in appropriately by them – The role of the ODNI, what it is and what it should be – The thesis that the US is about to enter and age of abundance and what this means for the US and the world – What CEOs need to know about geopolitical risk

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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 Fellowship which attracted a lot of attention and detractors with a grant program that paid $100k to college aged students to skip the degree and work on passion projects. Michael followed this up with the formation of a venture capital fund that had a comparable investment thesis and has successfully invested in entrepreneurs emerging through unexpected channels and without college degrees.

Michael's book, and this conversation, resonated with me as I can't escape the feeling that he is onto something pointing out the declining value and increasing cost of a college education, but also his thesis that a new period of innovation is required and that the disruption will come from unlikely sources.

We take a deep dive into some of the areas requiring disruptive innovation and also a few of the exemplars from both the Thiel Fellowship and the 1517 fund. This conversation is a call for revolution in how we think about entrenched organizations and the potential for their inevitable decline.

Official Bio: Michael is co-founder and general partner at 1517. If the rust belt has come to define the hollowed-out industries of the Midwest, in the next ten years the paper belt will come to define the paper-based industries from Washington DC to Boston. In DC, they print money, visas, and laws on paper. In Delaware, companies incorporate on paper. In NYC, they print media on paper. And in Boston Harvard and MIT print diplomas on paper. Michael is dedicated to lighting the paper belt on fire.

Additional Resources:

Paper Belt on Fire book
Thiel Fellowship program
1517 Fund

Recommended Books:

Foster by Claire Keegan
The Waste Land: A Biography of a Poem by Matthew Hollis
Red Sparrow series by Jason Matthews

Paper Belt on Fire: How Renegade Investors Sparked a Revolt Against the University

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In this OODAcast, we talk with Jimmy Soni, the author of the book "The Founders: The Story of PayPal and the Entrepreneurs Who Shaped Silicon Valley". The Founders was one my Top 10 Security, Technology, and Business books of 2022, and is one of the few books I read last year that qualifies for each category.

Jimmy takes a deep, historical look at the founding story of PayPal with detailed analysis, interviews, and access that you won't find in any other telling of the PayPal story. PayPal is a fascinating company to look at, not only to examine the PayPal business, but in looking at what emerged out of the PayPal founding team in the future. A list of companies that includes the likes of SpaceX, Tesla, Affirm, LinkedIn, YouTube, Yammer, Palantir, Kiva, Yelp, and Yammer!

In the OODAcast we discuss:

PayPal's founding history
The unique cast of characters and the importance of understanding their origin stories
Key moments in PayPal's success
How PayPal is ultimately a hacker success story.

Podcast Version:

Official Bio:

Jimmy Soni is an award-winning author. His newest book, The Founders: The Story of PayPal and the Entrepreneurs Who Shaped Silicon Valley, was a national bestseller and received critical acclaim from The New York Times, Wall Street Journal, New Yorker, The Economist, Financial Times, and more. His previous book, A Mind at Play: How Claude Shannon Invented the Information Age, won the 2017 Neumann Prize, awarded by the British Society for the History of Mathematics for the best book on the history of mathematics for a general audience, and the 2019 Middleton Prize by the Institute of Electrical and Electronics Engineers. He lives in Brooklyn, New York, with his daughter, Venice.

Recommended Books:

The Founders: The Story of PayPal and the Entrepreneurs Who Shaped Silicon Valley

A Night to Remember

Paper Belt on Fire: How Renegade Investors Sparked a Revolt Against the University

The Founders: The Story of Paypal and the Entrepreneurs Who Shaped Silicon Valley

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In this OODAcast we interview one of our close friends and OODA network members, Jen Hoar.

Jen is a former journalist-turned-corporate investigator who has leveraged the potent act of asking, and listening, to turn strangers into sources and contacts into clients. Her expertise, which is clearly also her passion, is identifying and interviewing smart people about any given topic, to learn as much as possible to inform clients’ executive decision-making.

Harnessing her experience as a journalist and business intelligence practitioner, she has developed and delivered Human Intelligence for Business training for entrepreneurs, sales, private equity, business development and legal professionals. This training refines how to identify and contact knowledgeable people - prospective clients, partners, investors and subject matter experts - to harness unique insight from purposeful dialogue.

Official Bio:
Jen Hoar leads human source intelligence work at Forward Risk.

She specializes in — and loves — finding and interviewing smart people about any subject. A former journalist, Jen first honed investigative prowess at ABC News, National Journal, and CBS News, and later by working with former CIA operations officials and prosecutors, among others, in boutique corporate intelligence firms in the Washington, DC, area.

Jen was also a founding member of a Facebook investigative team, where she worked on election integrity and information warfare issues. A proud double Hoya, Jen is nonetheless endeared to Fordham, where her parents were longtime professors.

Additional Information:

Connect with Jen on LinkedIn

OODA Network Interview with Jen

Book Recommendation: Black Edge: Inside Information, Dirty Money, and the Quest to Bring Down the Most Wanted Man on Wall Street

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Covering technology issues, and specifically cybersecurity as a journalist is a tough endeavor. Some of these technologies are complex as are the security vulnerabilities often inherent in their deployment and making these topics broadly accessible can be a challenge. Many of the underlying issues touch upon national security and civil liberties creating an interesting nexus that must be highlighted in the proper context. Lastly, it can be a challenge to create trusted relationships with the hacker community, but they provide essential perspectives and leads.

Joseph Menn has established himself as one of the top journalists covering these issues for over two decades at organizations like the Financial Times, Los Angeles Times, Bloomberg, Reuters, and now at the Washington Post. He's spoken at conferences like Black Hat, Def Con, and RSA. He's written three books covering topics like Napster, cybercrime, and most recently the infamous hacker group cDC in his book "Cult of the Dead Cow: How the Original Hacking Supergroup Might Just Save the World".

In the OODAcast, Joseph provides insights from his career as a journalist covering technology and cybersecurity. We explore how he first got involved with Def Con Black Hat and the value of attending the events. Joseph discusses how he first got introduced to the cDC and why he decided to write a book about the group and developed an overall positive outlook in the critical role hackers will play in saving the world.

Official Bio:

Joseph Menn joined The Washington Post in 2022 where he specializes in computer security, hacking, privacy and surveillance. He has perhaps the longest running track record among professional journalists covering cyber security and cyber conflict issues, having over two decades of experience on the topic. Prior to the Washington Post he covered cybersecurity and technology for Reuters, the Financial Times and the Los Angeles Times

His books include "Cult of the Dead Cow: How the Original Hacking Supergroup Might Just Save the World" (2019) and "Fatal System Error: The Hunt for the New Crime Lords who are Bringing Down the Internet" (2010).

External Links:

Cult of the Dead Cow book

Joseph Menn on Twitter

Book Recommendation: The Dawn of Everything

Cult of the Dead Cow: How the Original Hacking Supergroup Might Just Save the World

The Dawn of Everything: A New History of Humanity

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Lawrence Gasman has researched and reported on quantum technologies from the beginning of the discipline of quantum computing. He is now the President of Inside Quantum Technology (IQT), which provides in-depth business intelligence for the quantum technology industry. IQT also runs several major quantum technology conferences as well as a quantum industry news service.

On this OODAcast we ask Lawrence to provide us with frameworks for understanding the state of quantum computing, quantum sensing, quantum security and the business around each of these major fields.

Discussion topics include:

How to explain the world of quantum effects to non technical leaders and what business leaders should know about the strange world of quantum physics.
The overall state of quantum computing today
How non-experts can know if a claim in a quantum computing project is valid or not.
A useful description of quantum sensing.
The importance of quantum security.
New NIST algorithms for improving quantum security.
The state of quantum R&D - what comes next in the quantum industry.

For more see: https://www.insidequantumtechnology.com

For more on quantum computing, quantum sensing and quantum security see the OODA Guide to Quantum Computing and Quantum Security Sensemaking

Related Reading: Explore OODA Research and Analysis Use OODA Loop to improve your decision making in any competitive endeavor. Explore OODA Loop

Decision Intelligence The greatest determinant of your success will be the quality of your decisions. We examine frameworks for understanding and reducing risk while enabling opportunities. Topics include Black Swans, Gray Rhinos, Foresight, Strategy, Stratigames, Business Intelligence and Intelligent Enterprises. Leadership in the modern age is also a key topic in this domain. Explore Decision Intelligence

Disruptive/Exponential Technology We track the rapidly changing world of technology with a focus on what leaders need to know to improve decision-making. The future of tech is being created now and we provide insights that enable optimized action based on the future of tech. We provide deep insights into Artificial Intelligence, Machine Learning, Cloud Computing, Quantum Computing, Security Technology, Space Technology. Explore Disruptive/Exponential Tech

Security and Resiliency Security and resiliency topics include geopolitical and cyber risk, cyber conflict, cyber diplomacy, cybersecurity, nation state conflict, non-nation state conflict, global health, international crime, supply chain and terrorism. Explore Security and Resiliency

Community The OODA community includes a broad group of decision-makers, analysts, entrepreneurs, government leaders and tech creators. Interact with and learn from your peers via online monthly meetings, OODA Salons, the OODAcast, in-person conferences and an online forum. For the most sensitive discussions interact with executive leaders via a closed Wickr channel. The community also has access to a member only video library. Explore The OODA Community

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In 2020, we launched the OODAcast video and podcast series designed to provide insightful analysis and actionable intelligence to decision makers. In this 100th episode, co-hosts Matt Devost and Bob Gourley review some of the key insights from the series. Matt and Bob also discuss a OODA's recent assessment of risks and opportunities given the geopolitical and technological environment, leading to a discussion of recommended actions for C-suite leaders.

We start with a review of an OODAcast episode which had deep personal meaning for the team, and opportunity to hear directly from one of John Boyd’s peers, Chet Richards. Chet was in the room when it happened, there as Boyd coalesced his OODA concept into the model for decision-making known around the world today. Chet was also the guy Boyd turned to to create the first sketch of the OODA loop. In his OODAcast Chet also revealed a little known fact about how Boyd influenced the famous business strategist/author Tom Peters. For many of us the OODA model has always been aligned with ways to thrive on chaos and now we know the roots of Peter’s concepts.

Another icon from the past we had the pleasure of talking with is retired Admiral Bobby Ray Inman. Bob described him as the mentor to his mentors. He articulated leadership lessons in a succinct list that is still being shared around the intelligence community today. In our discussion he provides context on key guidelines in his list, and adds a new one he wishes he would have codified many years ago.

A more recent leader we extract actionable insights from is John Chambers, the legendary former CEO of Cisco. He is on a mission to use technology to build a more equitable and open society and is investing in disruptive startups to help do that. His leadership lessons for large and small firms both are reflected in this session. He also provides predictions for 2022 and beyond that are so far coming completely true.

Another famed CEO and author is Kevin Roberts, the author of 64 shots. The book was extremely helpful to Matt during career transitions and is inspiring to any who are building companies. One of the many points he discussed was the need for an extreme proactivity, what he referred to as hacking into the future. He also provided an inspired description of how leaders should lead by putting their boots on and getting directly engaged with the true nature of their business.

Nate Fick has been a leader in our ecosystem for years. He has always been the kind of extremely competent and capable executive that people from across multiple communities want to follow. Today Nate is in the confirmation process to become the first Cyber Ambassador for the US State Department, where he will have the portfolio of cyber policy and action globally. Watch his OODAcast and you will get a feel for his spirit and approach to the world that includes many elements of leadership first examined by Marcus Aurelius.

Ric Prado has been described as the closest thing the US has to James Bond. Catchy, but we really know Ric and have to tell you, he is far smarter, savvy, fit and ethical than any portrayal of Bond. His OODAcast was the first time he agreed to speak publicly about his journey from a street smart kid to a CIA operator to a leader of HUMINT for the nation. After his OODAcast, Ric landed a book deal and become a best-selling author. His book Black Ops hit number 7 on the New York Times bestseller list and also hit #1 in several popular Amazon categories.

Following a review of these and other top picks, Bob and Matt transition to an overview of global risks and opportunities you will not want to miss (members seeking additional information including details on what to watch for next in the domains of geopolitical, technological and cyber risks see the OODA C-Suite Report).

OODAcast guests have written over 30 books. We invite you to check them out in this Amazon List.

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While the OODA Loop was been heralded in the domain of conflict, we often find the concept in business and there is no greater business analogy to dogfighting that David Greenberg's experience as a trader on the floor of the world's largest physical commodities exchange. David's job required rapid decision making based on constantly changing information and the mental fortitude to move onto the next decision and rapidly learn from both successes and mistakes. In addition to his work as a trader, David also guided the New York Mercantile Exchange (NYMEX) through its largest period of growth and through a digital transformation.

In this OODAcast, David shares his story and talks about how to make decisions in complex environments, but also developing the mental resiliency to deal with rapid change and impactful mistakes. David also shares his experiences from 9/11 and how one tiny circumstance saved his life and re-focused his energy on helping others.

Full bio:
Mr. Greenberg is the President of Greenberg Capital. He served as an Executive Board and Board Member of the New York Mercantile Exchange (NYMEX). He oversaw a decade of its largest growth from $800 million to $12 billion. Notably, at the time it was the world’s largest physical commodities exchange. While at NYMEX, David was the Chairman of the Corporate Governance, Marketing, International Expansion, Electronic Trading and Security Committees.

Mr. Greenberg’s twenty years as President of Sterling Commodities shaped the firm into one of the largest local clearinghouses at NYMEX.

Mr. Greenberg served as Director of Development for Executive Education at Florida Atlantic University. As a seasoned speaker, he has graced the podiums of the country’s most prestigious colleges and universities: West Point Military Academy, Columbia Business School, New York University, Syracuse University’s Whitman School of Business and Sacred Heart University’s Jack Welch School of Business.

He currently serves on the Executive Committee of Junior Achievement of South Florida and the Leadership Council for the United Negro College Fund of South Florida. Mr. Greenberg is a graduate of Connecticut’s Suffield Academy, where he later served on the board. David is a graduate of Syracuse University.

In addition to his successful career in significant advisory capabilities, he is a globally renowned and noted market analyst and media contributor. Having appeared on CNN, Fox Business News, Bloomberg and CNBC, Mr. Greenberg is often quoted on times such as the present. Mr. Greenberg’s expert opinions can be found in The Wall Street Journal, Bloomberg, The Financial Times and other publications.

Additional Resources:

https://www.instagram.com/tradingshrink/
https://daviddouglasgreenberg.com/

Recommended Book:

Raven Rock by Garrett Graff

Raven Rock: The Story of the U.S. Government's Secret Plan to Save Itself--While the Rest of Us Die

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John Spencer is a writer, thinker, speaker scholar who currently serves as the Chair of Urban Warfare Studies at the US Military Academy. He brings the experience of a veteran who has led in combat to his work, and in his latest book, Connected Soldiers, also provides insights from his time as a stay at home parent as his wife deployed. His analysis of connectivity and ints impact from multiple angles makes his book a very well rounded examination of how the Internet age is transforming how nations go to war.

In this OODAcast we discuss the book as well as John's career and insights he has for leaders, including leaders in business. We examine:

The US Army Rangers, their mission and spirit and ability to focus
How lessons in leadership from John's early career informed his leadership in combat
Boredom in war and how soldiers fill down time and how connectivity and new technology is used in down time
Ways connectivity and gaming impacted soldiers under John's command in combat
What it was like for John to be a stay at home dad when his wife deployed and how connectivity impacted that experience
Unit cohesion and unit motivation and lessons relevant beyond the military
Lessons from history being repeated in the Ukraine situation.
John Boyd and the OODA Loop as an example of studying our own way of thinking and seeking to learn better and optimize decision making

For more see:

John Spencer Online

Connected Soldiers

The Modern War Institute

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Duyane Norman spent nearly 30 years in the CIA with three Chief of Station and multiple other tours in a variety of interesting geographies and also had a focus on technology issues serving as Deputy Director of the Office of Technical Service within CIA’s Directorate of Science and Technology, and as a member of the CIA Counterterrorism Center’s Incident Response Team. Duyane established a reputation as an innovator and a disruptor looking for ways for the intelligence services to flourish given the fast pace of technological change and the dynamic threats emerging on the global landscape. In this OODAcast we discuss his career in the CIA, how the agency must adapt over time, and the role disruptive technology will play in the geopolitical landscape. We also talk about his Station of the Future project and how that can serve as a roadmap for future innovation.

Official Bio:

Duyane R. Norman retired from CIA in March 2019 as a member of
the CIA’s Senior Intelligence Service with 28 years of distinguished service. He currently leads the Defense Innovation Unit’s engagement with the Department of Defense’s Agencies and
Activities and serves as DIU’s link to the Intelligence Community. He is the District of Columbia Chairperson for the National Board of State Funeral for World War II Veterans and an occasional consultant to a range of government agencies and private companies.

Mr. Norman has substantial leadership, operational and technical experience across a broad spectrum of military and government. He is a recognized leader in innovation, having founded and led the Central Intelligence Agency’s Station of the Future Program. He served seven overseas tours in the Directorate of Operations, in Central and South America, Central Asia, the Balkans, the Caucasus and Middle East, including three tours as Chief of Station and one tour as a War Zone Chief of Base. He served multiple assignments at CIA Headquarters including Chief of Operations for Latin America Division, with oversight and responsibility for all CIA operations in Latin America, as the Deputy Director of the Office of Technical Service within CIA’s
Directorate of Science and Technology, and as a member of the CIA Counterterrorism Center’s Incident Response Team.

Mr. Norman earned a BA in Latin American Studies from Vanderbilt University. He speaks Spanish, Portuguese and Russian.

Book recommendations:

Ghost Fleet

Flashman series

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Greg Touhill is one of the nation’s premier cybersecurity, information technology and risk management leaders. As an Air Force officer he led technology efforts in some of our nation's most demanding organizations including combatant commands during time of war. He is an accomplished speaker and author and business executive and also served as our nation's first Chief Information Security Officer (CISO).

Touhill is currently the director of the Carnegie Mellon University Software Engineering Institute's CERT Division. In this capacity he leads one of the most highly regarded organizations in the cybersecurity community. The CERT is a diverse group of researchers, software engineers, security analysts and digital intelligence specialists who work together to research vulnerabilities, contribute to long term changes and develop cutting-edge information and training to improve the practice of cybersecurity.

In this OODAcast we examine Greg's approach to leadership and then get into:

Operational views of the cyber threat that can help drive collective action in mitigating risks.
Ways security leaders can continue to learn and grow
The CERT's role in improving security through cybersecurity
Lessons learned in communicating security topics with non technical audiences (including a fantastic discussion of lessons from SciFi)

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In this OODAcast, we interview Ron Gula, co-founder and CEO of the highly successful Tenable Security(NASDAQ:TENB) and currently President of Gula Tech Adventures. Ron has a long history in the cybersecurity field that includes starting his career as an NSA hacker and then transitioning into an entrepreneur responsible for multiple innovations in the market and several successful companies. Ron remains a hacker at heart, and currently focuses his energy on investing in and mentoring emerging companies, improving public awareness on cybersecurity, and engaging in philanthropic efforts. In our conversation with Ron, we explore his career history, the state of cybersecurity, where we should focus our innovation investments, and how cybersecurity professionals can help solve not just global problems, but get engaged in local solutions at scale.

Ron is President at Gula Tech Adventures which focuses on cyber technology, cyber policy and recruiting more people to the cyber workforce. Since 2017, GTA has invested in dozens of cyber start-ups and funds and supported multiple cyber nonprofits and projects. Ron started his cybersecurity career as a network penetration tester for the NSA. At BBN, he developed network honeypots to lure hackers and he ran US Internetworking’s team of penetration testers and incident responders. As CTO of Network Security Wizards, Ron pioneered the art of network security monitoring and produced the Dragon Intrusion Detection System which was recognized as a market leader by Gartner in 2001. As CEO and co-founder of Tenable Network Security, Ron led the company’s rapid growth and product vision from 2002 through 2016. He helped them scale to more than 20,000 customers worldwide, raise $300m in venture capital and achieve revenues in excess of $100m annually. Ron is President at Gula Tech Adventures which focuses on investing and advisement of two dozen cyber-security companies. Ron was honored and humbled to receive the 2017 Betamore BETA award, be named a 2016 Baltimore Tech 10 leader and a 2013 Maryland entrepreneur of the year by Ernst and Young.

Additional Resources:

Gula Tech Adventures

Ron on Twitter

Book recommendations:

Shards of Earth

A Big Ship at the Edge of the Universe

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In this OODAcast, we talk with Jim Lawler who is a Senior Partner at MDO Group, which provides HUMINT training to the Intelligence Community and the commercial sector focused on WMD, CI, technical and cyber issues. Mr. Lawler is a noted speaker on the Insider Threat in government and industry. Prior to this, Mr. Lawler served for 25 years as a CIA operations officer in various international posts and as Chief of the Counterproliferation Division's Special Activities Unit. We talk with Jim about his career in intelligence and national security, his views on the current threats including some of his fictionalized accounts in his novels, and his most notable intelligence operation; the A.Q. Khan nuclear takedown.

Mr. Lawler was a member of CIA's Senior Intelligence Service (SIS-3) from 1998 until his retirement in 2005. He was a specialist in the recruitment of foreign spies, and he spent well over half of his CIA career battling the proliferation of weapons of mass destruction. As Chief of the A.Q. Khan Nuclear Takedown Team, which resulted in the disruption of the most dangerous nuclear weapons network in history, Mr. Lawler was the recipient of one of the CIA's Trailblazer Awards in 2007, marking the 60th anniversary of CIA. In 2004, former DCI George Tenet sent Mr. Lawler a note which stated, “Jim, what you and your team have achieved will rank up there as one of the most spectacular intelligence accomplishments in the history of the CIA. It occurred because of your exemplary leadership. Not only are we in the process of taking down a network, we are also in the process of disarming a country as a result of your fine work. With respect, George J. Tenet” And former DDCI John McLaughlin noted that the effort was “the closest thing I’ve ever seen to a perfect intelligence operation.”

Mr. Lawler also received the Director's Award from DCI George Tenet, the U.S. Intelligence Community's HUMINT Collector of the Year Award, and the Donovan Award from the CIA's Deputy Director of Operations.

He is a graduate of Rice University, Houston, Texas; and the University of Texas School of Law. He is married to Ellen and has three children and seven grandsons. He has completed two novels: “Living Lies,” an espionage story of the Iranian nuclear weapons program, and “In the Twinkling of an Eye,” about recruiting a spy at the heart of a devastating covert Russian-North Korean genetic bioweapons program. Both have been cleared by the CIA’s Publication Review Board and are to be published in 2021. He is currently writing his third espionage novel, “The Traitor’s Tale,” which is about treachery and treason deep within the CIA.

Additional Resources:

Jim's book Living Lies

Book Recommendations:

The Recruiter
First Casualty
Slow Horses

The Recruiter: Spying and the Lost Art of American Intelligence

First Casualty: The Untold Story of the CIA Mission to Avenge 9/11

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Alyssa Miller is a life-long hacker and highly experienced security executive who has a passion for security and the security community. She is an excellent advocate for continuous improvement in the community and a frequent speaker to audiences of both fellow business leaders and security community audiences. This combined with her deep experience in the industry makes her the perfect person to research and write the Cybersecurity Career Guide. The guide is a much needed resource for our community.

In this OODAcast we ask Alyssa for context of use to cybersecurity professionals, including discussing insights important to those just starting out, those seeking to continue their self improvement journey, and those seeking to laterally move into the community. In the discussion we also capture the fact that the book is also a great resource for the most experienced cybersecurity professionals, since these more senior individuals are frequently asked for mentorship and other career advice and will find this to be a good source of current insights.

We seek to go beyond the advice in the book and believe you will find this interview and excellent window into the decision-making processes and perspectives of Alyssa. The attitudes and approaches of a hacker, including those great traits of curiosity, persistence and continuing self education are apparent and an example for us all.

The book is available now for pre-order and purchasing at this link will enable an advanced electronic copy for review: Cybersecurity Career Guide

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This OODAcast is a special edition focused on profiling Russian President Vladimir Putin with Dr. Scott Shumate, who has over 30 years of experience evaluating national leaders, terrorists, spies, and insiders. Scott shares his unique perspective's on Putin informed by his extensive experience and insight. During this session we explore:

Is Putin suicidal?
Is Putin a rational actor?
How would Putin feel about an escalatory use of cyber attacks?
What is Putin's primary motivation in attacking the Ukraine?
How does Putin value propaganda?
Should we expect more nuclear bravado from him?
Is he a narcissist?
Plus lots of additional insights...

OODA Loop members can find our quick summary of this profile here (Link)

R. Scott Shumate is the president of Valutare, LLC. He has overseen contracts with the Department of Defense, the Federal Bureau of Investigations, the Secret Service, and the Department of Homeland Security.

Scott worked for 19 years as an undercover operations officer, psychologist for the Central Intelligence Agency, he is seen as an expert in Counterterrorism, Middle Eastern, South-East Asian, Euroasian cultures including Russia and Chinese cultures. Scott left the Agency in 2003 to Join the Department of Defenses, Counterintelligence Field Activity as a Senior Executive where he led a multimillion-dollar Behavioral Sciences program that infused operational guidance to FCI programs as well as investigations.

Currently, Dr. Shumate has developed a new and creative Insider Threat program that uses big data to analyze metadata on a network that uses Context and Motivational analysis. The model is based on an offensive recruitment, crime and changes in the person’s environment. Through Valutare, he provides Counter-Surveillance, Elicitation, and Interviewing training as well as TSCM scanning.

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In this OODACast, Matt talks with Chris Butler about how concepts like adversarial thinking can be applied to product design and management. Chris is an exemplar of someone who has excelled in his field but also looks to study and bring disruptive ideas like randomness and future framing from other disciplines to determine their value and applicability in product management. As it turns out, he's a big fan of John Boyd's OODA Loop and even made a trip to the Boyd archives where he discovered that Boyd was a fan of a certain science fiction book. Chris Butler is a chaotic good product manager, writer, and speaker. He facilitates critical decision making for teams that build new and innovative products. Chris focuses on bias, uncertainty, and randomization to help build robust and resilient teams. He has over 20 years of product management leadership at Microsoft, Waze, KAYAK, and Facebook Reality Labs. He is now Assistant Vice President, Head of Product Operations, at Cognizant where he PM's the PM experience. Additional Information: Book Recommendation: Why Greatness Cannot be Planned https://amzn.to/3tvkIeN Chris on LinkinedIn: https://www.linkedin.com/in/chrisbu/ Chris on Twitter https://twitter.com/chrizbot Chris on YouTube: https://www.youtube.com/playlist?list=PLTR1CgetbclHfZvNAR8BTCpA5Hz9qFxqf
Chris on Medium https://chrizbot.medium.com/

Why Greatness Cannot Be Planned: The Myth of the Objective

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John Chambers is the legendary former CEO of Cisco, a company he helped grow from $70 million in revenue per year when he joined in 1991 to $1.2 billion a year the year he became CEO to over $48 billion a year by the time he retired in 2015. As a leader John was always known for far more than just revenue growth, he was skilled at building an organization that treated people well, including employees, customers and the community.

In this OODAcast we discuss John's book, Connecting The Dots, which shares his insights into leadership including leadership of organizations that need to disrupt themselves. The lessons of this book can help those at any stage of a career improve in their ability to lead innovative companies. John speaks to many learning points in his career including early lessons on how governments and companies ignore transitions at their own peril. He draws lessons from lost opportunities that include things West Virginia could have done differently, as well as transitions missed by IBM and Wang.

We asked John to elaborate on his ability to spot market transitions and assess how they should impact business strategy and operations. This is a skill we are always seeking to improve at OODA and found his recommendations very consistent with our methods of keeping our ear to the ground and seeking insights from multiple sources, then dealing with reality as it is, not as you hope it will be.

We also ask John for his assessment into the changing economic situation because of the pandemic. We discuss how his projections at the beginning of the pandemic played out. We then get his assessment on what is in store for the coming months, resulting in advice which should be heard by any CEO seeking to serve. He tells us agility, a word he used to dislike because it sounded like marketing, now needs to be the mantra of every CEO.

"Agility is the watchword for leaders today"

John is currently the CEO of JC2 Ventures, a venture capital firm he founded to invest in and mentor startups he believes are positioned to become core drivers of economic growth and job creation in the digital age. We discuss his approach on finding these firms and mentoring them. The CEO of a key firm in his portfolio, Guarav Banga of Balbix, was interviewed for the OODAcast last year).

John concludes with advice for any leader seeking to succeed:

"You deal with the world the way it is, not the way you wish it was."

He also reminds us all that

"The winners are those that do not do the right thing for too long. The winners are those that are willing to disrupt themselves."

Connecting the Dots: Lessons for Leadership in a Startup World

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In this OODAcast, we talk with Simon Clark. Simon a British journalist and writer. He previously worked at the Wall Street Journal. His investigative reporting has led him to the poppy fields of Afghanistan, the copper mines of Congo and to many banks in the City of London. He was nominated for a Pulitzer Prize in 2016.

Simon is the author of the "The Key Man: The True Story of How the Global Elite Was Duped by a Capitalist Fairy Tale ". The book tells the story of Arif Naqvi and his Dubai-based private-equity firm Abraaj and how he attracted billions of dollars in investment and shared the stage and social scene with the world's global elite in what would become one of the most audacious large scale frauds of recent times. The book also made my Top 10 Security, Technology, and Business book list for 2021.

We discuss the rise and fall of Arif and specifically look at the tragedy of root causes that shifted Abraaj from the beacon of emerging economy investments to a shell game of alleged deep investor fraud. We also spend time discussing why Arif was able to attract so much attention and the role transparency could have played in discovering the fraud sooner.

Podcast Version

Simon's Book:

The Key Man: The True Story of How the Global Elite Was Duped by a Capitalist Fairy Tale

Book recommendation:
Empire of Pain: The Secret History of the Sackler Dynasty

The Key Man: The True Story of How the Global Elite Was Duped by a Capitalist Fairy Tale

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Charity 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.

Additional Resources:

China’s Digital Colonialism

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Jan Chipchase is the founder and director of Studio D Radiodurans, a research, design and innovation consultancy. He specializes in identifying nuanced patterns of human behavior. The insight it generates informs and inspires design, strategy, brand and public policy.

Jan describes his work in design anthropology in terms of a satellite launched into space that is chartered with identifying new planets, existential threats, but with a lens that can also be turned back on earth to help his clients also understand themselves.

I've been fascinated with Jan's work for quite some time and had previously read and recommended both of his books. His research provides great insights into how products are being intentionally and unintentionally used and often take him into gray market environments.

In this OODAcast, we discuss Jan's work but also his insights into how to conduct field research, build focused teams, and what sorts of insights can be derived. He also shares some great OODA Loop stories where quick decision-making and disrupting expected behaviors allowed him to get out of some tight situations.

Earlier in his career he was Executive Creative Director of Global Insights at frog, a global design and innovation consultancy, where he headed up the global research practice. Prior to that he was Principal Scientist at Nokia where he specialized in entry level products. He's worked on products that have collectively sold over a billion units.

His first book Hidden in Plain Sight was published in English, Japanese, Chinese, Korean and Russian. It became a best-seller in South Korea, of all places. The follow-up Today’s Office was published in South Korea. He also wrote The Field Study Handbook.

At various times he has been based out of London, Shanghai, Los Angeles, San Francisco, Berlin and a decade in Tokyo.

Additional Links:

Studio D Radiodurans

Jan's Books:

Hidden in Plain Sight

The Field Study Handbook

Book Recommendations:

The Culture Map
Living in Data
Sensemaking in Organizations

Sensemaking in Organizations (Foundations for Organizational Science)

Hidden in Plain Sight: How to Create Extraordinary Products for Tomorrow's Customers

Living in Data: A Citizen's Guide to a Better Information Future

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Ben Dubow is CTO and founder of Omelas, a firm that provides data and analysis on how nations manipulate the web to achieve their geopolitical goals. He has a background in research on Russian and Chinese online information operations and is a recognized expert, having appeared on international media including Reuters, Bloomberg and Roll Call. Ben began his career tracking jihadi, white supremacist, and Iranian activity online before joining Google where he played a lead role in removing ISIS content from YouTube and establishing the Redirect Method to counter violent extremism. Before Omelas, Ben was Secretary of Code To Inspire, a nonprofit that teaches Afghan women to code. Ben speaks Arabic, French, Farsi, and basic Russian.

In this OODAcast we discuss Ben’s continuous drive to work in meaningful ways by contributing technical and cultural expertise to emerging challenges. Other topics include:

The foundational story of Omelas and the needs for technology to help spot malicious influence operations via tracking open source information.
How to focus on missions by understanding what decision-makers need
How authoritarian states manipulate open source data
Why propaganda is effective and how the right information can help counter it
How technology can improve scale of analysis
The Omelas Wolf Totem dashboard and what it presents
The metrics that can be applied to malign influence operations
How to reduce the risk of our own analysts being biased in research

Additional Links:

Omelas

https://www.benjamindubow.com/

Book recommendations:

The Constitution of Knowledge: A Defense of Truth

The Invention of Russia: The Rise of Putin and the Age of Fake News

The Invention of Russia: From Gorbachev's Freedom to Putin's War

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In this OODAcast we talk with Jahon Jamali of Sarson Funds about a range of cryptocurrency issues including his coming book Deep Crypto. We also dive deep into the coming Metaverse.

Jahon Jamali is a leading expert on emerging technologies, global risk management and international relations. He began his career as a U.S. Intelligence Officer with the Defense Intelligence Agency. He also has extensive experience in the high tech community creating and growing startups through to successful exits. All this makes him an even more credible authority when it comes to seeking the trends that are moving technology, business and government operations forward.

This discussion examines the role of Bitcoin and Ethereum in finance today and the especially important need for cryptocurrencies to provide a trust layer for the Internet. Think of this trust layer in the context of the coming metaverse. As Jahon makes clear, there have been great visions of a metaverse for years, but something has been missing: a trust layer. Jahon also builds a very compelling logical argument that free loving countries open societies should really embrace cryptocurrencies like Bitcoin and Ethereum. Dictatorships and kleptocracies hate cryptocurrencies. This is a big reason he is quick to point out, in case there is any mistake, that “cryptocurrencies are as american as apple pie.”

Some of the topics we cover include:

Money as a belief system and the current status quo of money
The need to shift concepts of money and the need for trust
Jahon's experience educating large financial institutions on the nature of cryptocurrencies
The state of maturing cryptocurrency community
What an immutable distributed ledger can do for establishing a foundation of trust
The shifting of importance of geographical boundaries
What everyone (yes everyone) needs to know about cryptocurrencies
The waking up of governments, including state, local, and even national governments to crypto
Some of the naysayers and arguments against the Metaverse and Cryptocurrencies

The OODAast with Jahon makes it very clear, he is a great explainer of topics like these, which makes us very eager to see the book Deep Crypto. Pre-order yours at: Discovery Deep Crypto

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Maury Rogow builds a solid case that your brand will live or die based on the story you tell in the metaverse.

Maury is a pioneer in applying the art of storytelling to convey the value of technology in the Internet age. He built a successful approach to storytelling that made direct contributions to the success of some of the most important firms in the early wave of Internet companies. He later leveraged storytelling expertise and insights into a career in Hollywood which included producing films and helping craft storylines. After six years in Hollywood he shifted focus to how to help major brands tell their stories. His company Rip Media Group has helped companies from multiple sectors of the economy leverage the mobile Internet and video to improve their marketing and storytelling.

Today Rip Media Group, is preparing for another big shift, the transition to the age of the Metaverse. In this OODAcast we dive deep into how Maury sees the Metaverse shaping corporate strategies and ways leaders should be positioning themselves to serve the early adopters of the coming Metaverse.

What does Maury see coming?

The metaverse is the third big wave of change to sweep across the Internet. The first was the client server world of the initial Internet. Then the video mobile world of the last decade. Now the metaverse promises to be just as, or maybe even a bigger change than those first two shifts.

Maury encourages us to think of the Metaverse today as an infant, so new that it is hardly functional yet. But there is enough there to see something incredible is coming. Those that are grasping the power and potential of the coming metaverse today are those that are probably interacting with large online communities like those around the big 3D games. There are other use cases including medical, healthcare, industrial and retail already coming into focus. But all are in their infancy. The real power of the Metaverse will come when users will have persistence across multiple platforms including an ability to exchange value and be productive.

An example of a retail metaverse is RedFox, which has built a shopping mall which enables retail, entertainment, interaction with others and a blended approach to purchasing that bridges the virtual and real worlds.

We discuss retail and the huge economic potential for retail in the metaverse. We also discuss how just becoming part of the metaverse is not going to guarantee success. It will take marketing and advertising that helps people understand why to visit an online destination. Maury has crafted campaigns for metaverse companies already, and has found success by building stories that leverage timeless storytelling practices. When it comes to marketing to bring attention to metaverse capabilities, he describes his methods with an acronym that helps people understand the importance of action. The acronym is STUFF, which stands for:
1. The sizzle and sexy elements of a story
2. Touching or nostalgic story
3. Unexpected or unique
4. Funny
5. Fear of something

We dive into several use cases other than retail, including how metaverse enabled technologies are already helping in delivery of healthcare. The use of the metaverse for testing and training for the military, the use of the metaverse for education, real estate, legal advice, and business planning was also examined.

Maury and Bob discuss views on the great SciFi stories that have helped people understand the potential of the metaverse, including Snowcrash, Neuromancer, Enders Game, Ready Player one. SciFi stories can help conceptualize potential benefits and also potential pitfalls and problems. One example of the latter is conceptualizing security challenges, something rarely discussed these days. Bob mentions two SciFi stories that can help us think through security issues related to the metaverse, one from Star Trek (Kirk hacked the Kobayashi Maru scenario) and one from Ready Player One (there was a credential theft scene). Bob and Maury discuss the "so-what" of potential security issues in this domain. Clearly as we build our metaverse we really have to think about security, privacy and counter crime.

Maury’s advice for corporate metaverse strategies:

We are early. Which is good! Get involved nad keep a watchful eye on the space
The worst decision you can make is to do nothing.
As you build your metaverse strategy, build your communication strategy and know how you are going to tell your story across the brand.

Related Resources:
Rip Media Group

Maury Rogow on LinkedIn

The Metaverse at OODAloop

The Metaverse Is Coming And It Will Disrupt The Current Internet

The age of the Metaverse is upon us. The Metaverse is the successor to the Internet of today. It is a future state that will include persistent interoperable virtual worlds and the platforms required to support and interact with them. It will have its own thriving economy and deliver experiences unavailable in the physical world. It will be a primary means of educating our youth and delivering knowledge through life, and will be a leading form of social interaction and entertainment. For more see: What To Know And Do About The Coming Metaverse

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Alan Cohen is a partner at DCVC, a highly regarded venture capital firm who pioneered the concept of investing in Deep Tech.

Alan has helped lead and grow some of the most influential enterprise IT companies in the world. This includes serving as a VP of Enterprise for Cisco. He has also advised companies like Box, Cohesity, Netskope and Mobile Iron. He has been on the leadership teams of breakthrough companies like Nicira and Illumio.

At DCVC he tracks innovations across multiple sectors of the economy and helps steer investments. He also sits on the boards of several DCVC portfolio companies, many of which we talked about in this OODAcast.

We certainly talk tech with Alan, and he is the perfect guy to examine some of the more exciting breakthroughs being achieved through Deep Tech investing. But were pleased to learn his foundational story was not in a high tech field. He was an avid reader as a child and for his education pursued an English undergraduate and then completed a Master of Arts in English. In our discussion it becomes clear his love for a good narrative story paid off in his ability to seek out the deeper meaning of tech and express its impact in the language of business decision-makers.

In our review of the narrative of Alan’s own career we suss out a significant lesson that informs his mental model for decision-making. There is a threat to good decisions, especially decisions in due diligence. This threat is the human mind’s ability to deceive itself, especially through confirmation bias. In Alan’s view, the hardest thing about being an investor or decision-maker is avoiding this confirmation bias. Things that make a person successful earlier in a career can be the things that trip you up at other stages. He sites Tony Soprano, who used to say ‘Remember when’ is the lowest form of conversation. Too much nostalgia leads to too strong of a confirmation bias.

Note: At the time of our interview with Alan one of the partners at DCVC had just returned from Space, having flown on the same Deep Blue flight with William Shatner. We discuss some of the relevance of this to technology innovation and leadership with Alan.

Some of the firms we discuss with Alan include:

Evolv: Applies sensors, data, and machine learning to detect and prevent a wide set of global threats to people.

Planet Labs: Planet uses over 150 of its satellites in orbit and powerful AI to image the entire Earth every day, making global change visible, accessible, and actionable.

Rocket Lab: Delivers a range of complete rocket systems and technologies for fast and low-cost payload deployment.

Capella Space: Persistent and reliable information from space independent of weather and light conditions using synthetic aperture radar.

Atomwise: Breakthrough products for pharma and agricultural companies with novel AI for atom-by-atom chemistry.

Recursion: Discovers transformative new life science treatments by applying breakthrough AI and computer vision to understand the behavior of millions of living human cells in parallel

Primer: Primer helps parse and collate a large number of documents across several languages

Illumio: stops cyber threats by dynamically enforcing segmentation and policy on every point of compute and storage, on premise or in the cloud, with lights-out, hands-free management.

Agility Robotics: Bi-ped humanoid robots to automate pick/place tasks in logistics.

Pivot Bio: Fueled by an innovative drive and a deep understanding of the microbiome, Pivot Bio is pioneering transformative advances in fertilizer and crop nutrition.

These are just a few of the Deep Tech firms the DCVC team has been investing in and helping grow. These and many others have already made direct positive benefits in terms of helping fight global warming, defeating pandemics, reducing death from terminal diseases and helping defend democracy from hostile threats.

For more see:

DCVC

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Our OODAcast with John Robb in June 2020 has proven to be one our most popular ever, so we were excited to host him for a second interview.

John is one of the most disruptive thinkers of our time and is capable of drilling down on critical issues like security, society, and technology with deep authority and insights.

In this OODAcast, we discuss a wide variety of issues:

The role that networked tribalism played in the election and the events of January 6, 2021, and what comes next.
The role algorithms, AI, and Machine Learning will play in creating and/or disrupting networked tribes.
The role emerging technologies will play in building a new data economy in which individuals establish digital self sovereignty and share in the value proposition of their data.
Bitcoin in El Salvador and new models for economic disruption, development, and prosperity.
How U.S. leaders suffered from OODA Shear in analyzing the dynamic situation in Afghanistan and the allure of framing the problem as Taliban 2.0 when we couldn't orient ourselves to ground truth.
The role wargaming and red teaming can play in developing leaders that aren't as susceptible to OODA Shear.
What is the Long Night? Is it inevitable, or can we work now to build resiliency against it?

Related Links:

OODAcast with John Robb in June 2020 where he discusses his background a variety of subjects.

The Global Guerrillas Report

John Robb on Twitter

John's Book Brave New War

Anathem (John's favorite book from the last year)

Brave New War: The Next Stage of Terrorism and the End of Globalization

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In this OODAcast we ask retired Admiral Bobby Ray Inman for insights into his approach to analyzing complex situation and managing intelligence efforts. Admiral Inman served in the Navy from November 1951 to July 1982, retiring with the rank of four star admiral, the first military intelligence officer to ever reach that rank. On active duty, he served as director of naval intelligence, then later director of the National Security Agency and as deputy director of Central Intelligence. After retirement Inman was chairman and CEO of the Microelectronics and Computer Technology Corporation (MCC) in Austin, Texas, for four years and chairman, president and chief executive officer of Westmark Systems Inc., a privately owned electronics industry holding company, for three years. Inman also served as chairman of the Federal Reserve Bank of Dallas from 1987 through 1990. He became a adjunct professor at The University of Texas at Austin in 1987 and was appointed a tenured professor holding the Lyndon B. Johnson Centennial Chair in National Policy in August 2001. He recently retired from that position.

Decades ago he codified his principles in a list of rules he used to teach and lead others with. They are still exchanged and studied by leaders today, and they provided a good framework for our discussion in this OODAcast.

Inman’s Rules

Conservation of enemies: Be slow to anger and quick to build allies
When you are explaining you are losing: In most cases trying to explain away something never convinces the listener and just wastes your time. Learn from your mistake and move on. Sometimes the same thought is captured by the adage: When in a hole stop digging
Something too good to believe probably is just that, untrue: This remains important not just in national intelligence but in fighting fraud.
Go to the Hill alone: Supporting governance processes are just too important.
Wisdom in Washington is having much to say and knowing when not to say it: Never overwhelm decision makers.
Never sign for anything
The only one looking out for you is you: Take personal responsibility for your actions.
If you think your enemy is stupid, think again: Arrogance results in failure and surprise.
Never try to fool yourself: Too frequently it is easier to deceive ourselves rather than believe reality
Never go into a meeting without knowing what the outcome is going to be.
Don’t change what got you to where you are just to get to the next place.
Intelligence is knowing what the enemy doesn’t want you to know: It is about stealing secrets, not reading the news.
Nothing changes faster than yesterday’s vision of the future: Don't try to simply predict, you probably need to conduct scenario planning over multiple futures.
Intelligence users are looking for what is going to happen, not what has already occurred: Intelligence is not about history. Just because history is easier does not mean it is the mission.
It is much harder to convince someone they are wrong than it is to convince them they are right: This observation leads to the important point that intelligence professionals need a high emotional intelligence and ability to convey the truth in ways that get it accepted even when it is not welcome.
For Intelligence Officers in particular there is no substitute for the truth.
By the time intelligence gets back to a user with the answer the question usually has changed: Especially in operational intelligence.
Always know your blind spots, get help to cover them.
You can never know too much about the enemy: Do not fear information overload, manage it.
Tell what you know, tell what you don’t know, tell what it means: This framework helps decision-makers contextualize insights into ways that make intelligence more actionable.
Tell them what you are going to say, tell them, then tell them what you told them, they might remember something.
Never have more than three points.
Never follow lunch or an animal act.
Believe is correct, intelligence officers never feel.
The absence of evidence is not evidence of absence: Be proactive and seek more insights on the situation
Boredom is the enemy, not the time to any briefing.
If you can’t summarize it on one page, you can’t sell it to anyone.
Always allow time to consider what the enemy wants me to think, is he succeeding or am I?
If you can’t add value, get out of the way.
Beware of mirror imaging: Thinking the adversary or others are the same as we are has contributed to most major strategic failures through the years, including the 20 year involvement in Afghanistan.

Related Reading: Black Swans and Gray Rhinos Now more than ever, organizations need to apply rigorous thought to business risks and opportunities. In doing so it is useful to understand the concepts embodied in the terms Black Swan and Gray Rhino. See: Potential Future Opportunities, Risks and Mitigation Strategies in the Age of Continuous Crisis

Cybersecurity Sensemaking: Strategic intelligence to inform your decisionmaking The OODA leadership and analysts have decades of experience in understanding and mitigating cybersecurity threats and apply this real world practitioner knowledge in our research and reporting. This page on the site is a repository of the best of our actionable research as well as a news stream of our daily reporting on cybersecurity threats and mitigation measures. See: Cybersecurity Sensemaking

Corporate Sensemaking: Establishing an Intelligent Enterprise OODA’s leadership and analysts have decades of direct experience helping organizations improve their ability to make sense of their current environment and assess the best courses of action for success going forward. This includes helping establish competitive intelligence and corporate intelligence capabilities. Our special series on the Intelligent Enterprise highlights research and reports that can accelerate any organization along their journey to optimized intelligence. See: Corporate Sensemaking

Artificial Intelligence Sensemaking: Take advantage of this mega trend for competitive advantage This page serves as a dynamic resource for OODA Network members looking for Artificial Intelligence information to drive their decision-making process. This includes a special guide for executives seeking to make the most of AI in their enterprise. See: Artificial Intelligence Sensemaking

COVID-19 Sensemaking: What is next for business and governments From the very beginning of the pandemic we have focused on research on what may come next and what to do about it today. This section of the site captures the best of our reporting plus daily daily intelligence as well as pointers to reputable information from other sites. See: OODA COVID-19 Sensemaking Page.

Space Sensemaking: What does your business need to know now A dynamic resource for OODA Network members looking for insights into the current and future developments in Space, including a special executive’s guide to space. See: Space Sensemaking

Quantum Computing Sensemaking OODA is one of the few independent research sources with experience in due diligence on quantum computing and quantum security companies and capabilities. Our practitioner’s lens on insights ensures our research is grounded in reality. See: Quantum Computing Sensemaking.

The OODAcast Video and Podcast Series In 2020, we launched the OODAcast video and podcast series designed to provide you with insightful analysis and intelligence to inform your decision making process. We do this through a series of expert interviews and topical videos highlighting global technologies such as cybersecurity, AI, quantum computing along with discussions on global risk and opportunity issues. See: The OODAcast

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Bob Bigman spent a career in the intelligence community. He was the CISO of the CIA where he was tasked with leading efforts to protect the nation's most sensitive secrets. He remains a practitioner. Since 2012 he has provided direct consulting services to CISOs, CIOs, CTOs and CEOs seeking to reduce risk and improve security programs. Through it all he has built a reputation for rapidly assessing the state of enterprise security programs and then working to build action plans to drive continuous improvement.

This OODAcast examines aspects of Bigman's approach to security that can inform you own approach. We also solicit his views on compliance and security checklists, metrics, and the state of the IT industry (he does not hold back on any of those!).

Some other topics we covered include:

His journey from history major to cybersecurity practitoner
His views on why some organizations are better mitigating risks that others
The importance of senior leadership in mitigating cyber risks
The role of the red team in cybersecurity
Advice for businesses that cannot afford a CISO
The state of cybersecurity in local and state governments
Why there are 1000's of cybersecurity technologies on the market today and what that says about the state of the IT industry
The virtues of the MITRE ATT&CK approach
Views on the future of cybersecurity