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The OODAcast: A guide to our first forty episodes

Matt Devost and I started the OODAcast in March 2020 as a way of highlighting insights and lessons learned from leaders and decision-makers in our network. At the time of this writing we have posted 40 episodes of the OODAcast, and continue production of one expert interview a week. We alert readers of the OODA Daily Pulse to each new edition of the OODAcast, but also encourage all to subscribe to the OODAloop YouTube channel so our latest will show up in your feed. Audio is also available as a podcast for any podcast player.

The vast majority of the content in these 40 episodes is timeless and will long be relevant to anyone who seeks to sharpen their decision-making skills or gain insights into dynamic, competitive markets.

Here is a short guide to our OODAcast episodes. This is an attempt to categorize the interviewers based on their background, but as you can imagine, we are trying to categorize people who defy all labels! Every one of these thought leaders has cut their own path to success. That said, we hope this categorization can help you make the best use of this incredible wealth of insight and knowledge. We categorize these episodes by:

  • The CEOs and Board Members of the OODA Network
  • Cybersecurity Professionals
  • National Security Decision-Makers and Strategic Thinkers
  • Due Diligence, Private Equity, Venture Capital and Financial Sector leaders
  • Enterprise Technology Leaders/Decision-Makers
  • The Big Thinkers, Authors and Analysts


The CEOs and Board Members of the OODA Network

Lou Manousos, CEO of RiskIQ: Elias (Lou) Manousos is a recognized expert in Internet security and fraud prevention. He has been developing and delivering enterprise protection technologies for more than 15 years. As CEO of RiskIQ, he has spearheaded a new approach that helps Internet, financial services, healthcare, media and consumer packaged goods companies protect their brands from online fraud. Elias is also co-chair of the Online Trust Alliance (OTA) Anti-Malvertising Working Group and is responsible for, the first and only public database documenting malvertising incidents on a continuous basis.

CEO of Percipient Balan Ayyar: Balan Ayyar is the Founder and CEO of, a Silicon Valley based artificial intelligence firm focused on delivering products and solutions for the most pressing intelligence and national security challenges. We have been tracking this leader for years and have watched him inspire many to achieve great things. His leadership in senior officer roles in the US Air Force (he is a retired Brigadier General) included tours in combat zones and commands back in the US, including at one point leading the entire Air Force recruiting system. His visionary leadership in the corporate world resulted in the creation of a new firm providing new AI capabilities that are already serving some of the most critical missions in the nation.

Scott McNealy, Co-Founder of Sun Microsystems: Scott McNealy was a co-founder and CEO of Sun Microsystems and has one of the longest-running tenures as the CEO of a Fortune 500 company in history. He was one of the few businessmen that played a critical role in the emergence of the Silicon Valley technology industry that exists today and is a highly sought after advisor for technology companies. Scott is an advisor to OODA LLC.

Paul Pagnato, CEO and Founder at PagnatoKarp and Author of The Transparency Wave: Paul Pagnato migrated from a career as a scientist looking for life in outer space to one of the top financial advisors in the U.S. with a keen eye for tracking innovation, exponential change, and other emerging global issues. He is also the author of the recent book, The Transparency Wave, which highlights the essential role that transparency plays in future innovation and entrepreneurial success.

Kevin Roberts on Leadership, Decision-making, and Focused Action: Kevin Roberts has had an illustrious career spanning many industries over numerous continents including serving as Chairman and CEO of Saatchi & Saatchi, one of the world’s leading creative organizations, where he had responsibility for the effectiveness of several of the world’s leading advertising budgets including for clients Toyota and Procter & Gamble. Today, his company Red Rose Consulting counsels business leaders and employees on creative thinking, marketing, and leadership.

Matt Devost on Hacking Entrepreneurship and Identifying Threats and Opportunities: In this OODAcast, the tables are turned as OODA Network Expert Jen Hoar interviews CEO Matt Devost and they discuss how Matt consistently identified new threats and opportunities by blending eccentric interests into a career as a serial entrepreneur and become an established expert on cybersecurity, counterterrorism, and technology issues.

Paul Kurtz, CEO/Cybersecurity Leader and Founder of TruSTAR: Paul Kurtz is an internationally recognized expert on cybersecurity and the Co-Founder and Chairman of TruSTAR. Paul began working on cybersecurity at the White House in the late 1990s. He served in senior positions relating to critical infrastructure and counterterrorism on the White House’s National Security and Homeland Security Councils under Presidents Clinton and Bush. After leaving government, Paul has held numerous private sector cybersecurity positions including founding the Cyber Security Industry Alliance (Acquired by Tech America), Executive Director of SAFECode, Managing Partner of Good Harbor Consulting in Abu Dhabi, and CISO of CyberPoint International.

Cybersecurity Professionals

Tony Cole of Attivo Networks: Tony is an icon in the cybersecurity community. He is known both as a practitioner and a thought leader helping businesses and governments understand their risks and prioritize mitigation actions. He brings his decades of cybersecurity experience to this OODAcast.

Phil Reitinger, CEO of the Global Cyber Alliance: Phil Reitinger has been been a pioneer in cutting edge concepts for reducing risks in cyberspace for years. He was a special assistant US Attorney in the late 1990’s, a time when high end nation state attacks were on the rise and the application of US law to help counter threats was in a nascent stage. He helped move the Department of Justice to more vigorous action in cyberspace as Deputy Chief of the DoJ Computer Crime Section. He was appointed to lead the DoD Cyber Crime Center, one of the nation’s most highly regarded computer crime forensics organizations. He would later serve as an executive at Microsoft and then return to government service as a Deputy Undersecretary of Homeland Security as that organization was assuming new roles in defense of the nation’s cyberspace. He would later direct the security activities of Sony as SVP and CISO. For the past four years Phil has been leading a non profit organization known as the Global Cyber Alliance (GCA). The GCA works on projects that seek to mitigate risks from the most prevalent cyber threats that individuals and businesses face. They develop and deploy practical, real-world solutions that measurably improve the security of our cyber ecosystem.

Operational Cybersecurity Leader Cameron Over: Cameron Over leads the Cyber & Privacy service line at CrossCountry Consulting. Cameron has extensive past performance in cybersecurity, including experience advising organizations with transforming their cybersecurity and privacy programs. Cameron has been in the field of information security since the late 90’s. From mid-high school, she was exposed to early network discovery techniques while interning with DoD agencies, and held a Top Secret security clearance for more than 15 years. She grew her career assisting countless agencies with their most pressing security challenges, including specialized skills and expertise in Unix and Linux operating systems, Domain Name Services (DNS), Cross-Domain systems handling highly classified data, and web server and application security. Cameron now leads a team at CrossCountry comprised of cyber risk management, privacy and data protection, cloud security, security architecture and engineering, and advanced cyber risk, including threat intelligence, threat modeling, and advanced attack emulation. The team has developed a Cyber Fusion Lab, proprietary to the firm, as a highly secure environment with which to conduct assessments, testing, and analysis.

Bobbie Stempfley of Carnegie Mellon University Software Engineering Institute: The leadership team at OODA have had the pleasure of working with and learning from Bobbie Stempfley since her leadership of the Department of Defense Computer Emergency Response Team (DoD CERT) after she established it in the late 1990’s. This OODAcast captures insights from Bobbie that can inform the action of leadership of corporate and government leaders alike.

Mark Weatherford On Leading Change As a CISO: Mark Weatherford is a widely known practitioner/leader in the cybersecurity field. He is a mission focused leader who builds teams and gets hard things done. His career included success in the US Navy as a cryptologist, leadership and management in a major defense integrator, CISO for two states (Colorado and California), CISO of the nation’s regulatory organization for our power grid (the NERC), head of security efforts for the newly formed DHS, and operational CISO roles and advisory board positions for several US corporations.

National Security Decision-Makers and Strategic Thinkers

Congressman Will Hurd: This is a wide ranging discussion that touches on issues of geopolitical risk, cybersecurity, cyber risk and ways to help ensure our nation is prepared to compete and win in an age of rapid technological innovation. Quantum Computing, Artificial Intelligence, Advanced Communications (5G) and other mega-trends of technology are examined, as well as insights into leadership in the modern world.

Strategist and Author Peter Singer: P. W. Singer is a strategist at New America and the author of a string of impactful and prescient books. His non fiction books (including Cybersecurity and Cyberwar, and LikeWar), have contextualized the new realities of the internet enabled conflicts we find ourselves in. His fiction, including Ghost Fleet, has provided interesting drama and stimulating entertainment while at the same time helping us all come to grips with hard issues we need to deal with. His latest book, Burn-In, is similarly a work of helpful fiction, providing entertainment and an enjoyable story that will keep you turning pages, while at the same time being helpful to all of us who seek to understand what tomorrow may bring so we can make better decisions about it today.

Jim Miller on Managing Policy in an Age of Constant Disruption and Dynamic Threats: Jim Miller has worked for four decades on a combination of private and public sector initiatives focused on addressing a wide variety of national security threats.  He has held numerous positions within the Department of Defense including serving as Under Secretary of Defense for Policy and has been awarded the DoD’s highest civilian award four times.

Rear Admiral Paul Becker, USN (ret) on leadership in the modern age: During his 30 year career as a naval intelligence officer he lead major operational intelligence efforts, rising to the position of Director of Intelligence (J2) for the Joint Chiefs of Staff. Upon retirement from the Navy he formed a consultancy delivering solutions and lessons learned around intelligence to corporate America. He is also a professor, teaching at the US Naval Academy and the University of Virginia.  Paul is renowned for his ability to translate military leadership principles into corporate pillars of performance, productivity and profit.

Technology Executive Lewis Shepherd: Lewis Shepherd, seasoned federal technology executive and a senior director of technology strategy at VMware for an interactive discussion on the actionable lessons we should all be learning from the current crisis but also how the events of today are shaping the future of technology.

Due Diligence, Private Equity, Venture Capital and Financial Sector leaders

JC Raby of Boston Meridian Partners: Boston Meridian is an innovative investment banking firm focused on providing strategic M&A advisory and capital raising services to fast growing private and small cap public growth companies. Since their founding in 2004 they have closed more than $6 billion in transaction value. We invited Boston Merdian’s co-founder and partner JC Raby on to the OODAcast do discuss his insights into the market today as well as his views on things companies can do to ensure they position themselves for the best possible transaction in the future. We also asked his advice for the strategic investor/buyer of firms including context on due diligence prior to an event.

Alsop-Louie Partner and Famed Tech Executive Bill Crowell on Technology Due Diligence: Bill has been a boss, mentor, friend and advisor to both Bob Gourley and Matt Devost through the years, and has long been a valuable member of our OODA Network. In this video we ask Bill for insights of use to firms seeking to evaluate a business prior to acquisition, specifically seeking to do a better technology due diligence assessment.

Andy Lustig On Legal and Due Diligence Support In The High Tech Era: Andrew (Andy) Lustig is a partner at the high tech law firm Cooley, where he focuses on private equity investments, mergers and acquisitions and the general corporate representation of high-growth technology companies in both the commercial and government marketplace. His practice includes a wide range of industry sectors including information technology, national security, cybersecurity, data analytics, software and telecommunications. He also represents a number of leading venture capital and private equity firms.

Kevin DeSanto On Due Diligence and M&A Transactions and Trust Based Networking: Kevin DeSanto is an investment banker delivering advice and execution assistance to high growth businesses preparing for M&A and financial transactions. His company, KippsDeSanto, has developed a reputation for trusted execution support for companies in government contracting, aerospace, defense and cybersecurity. He leads teams that advise senior management, boards of directors and shareholders.

Enterprise Technology Leaders/Decision-Makers

Former CIA CTO Bob Flores: Flores has a very interesting background where he has continued to build on his experiences and education in a way that makes him the exemplar CTO for many of us. With his degrees in statistics and years of volunteer work as an emergency responder he has a knack for quickly assessing complex situations. And his years of enterprise technology leadership have equipped him with an almost magical ability to assess technology and its relevance to enterprise missions.

Quantum Security Practitioner Jane Melia of QuintessenceLabs: Jane Melia of QuintessenceLabs, is a practitioner who has spent years helping create and bring to market advanced enterprise technologies. She also has a reputation for being able to explain the business impact of technologies in terms conducive to making operational decisions. This skill is a highly needed one in the domain of quantum effects.

Industry Executive and Serial Entrepreneur Henry Harrison, CTO of Garrison: Henry is a seasoned technology industry executive and serial entrepreneur who has spent the last ten years focused on cyber security both as an independent consultant and as Technical Director for Cyber Security at UK defense and security company BAE Systems. Henry’s previous ventures include a desktop videoconferencing startup, and he has been responsible for developing and selling advanced electronics solutions into governments, telecommunications companies and financial services organizations amongst other sectors.

Robert Fink on Lessons Learned From Using Data In Crisis Response: Robert Fink is on the leadership team at Palantir, where he has helped shape their approach to product design and architecture. He has also played major roles in ensuring the company stays focused on the mission needs of customers today, and, through shaping R&D, is helping ensure the company is better able to serve the needs of future customers and future missions.

Bradley Rotter On The Future Of Work, CryptoCurrencies, Quantum Computing and Leadership: Bradley Rotter is a visionary investor who has pioneered investments in many new alternative investments classes including having been an early backer of hedge funds in 1982 while speculating on the Chicago Mercantile Exchange. He was also an early investor in Bitcoin and other cryptocurrency ecosystems and at a dinner with OODA CEO Matt Devost in 2012 predicted Bitcoin would exceed the price of gold.

Courtney Bowman, Privacy and Civil Liberties Engineer: Courtney Bowman leads Palantir’s Privacy and Civil Liberties Engineering Team. In this capacity he works extensively with local, state and international governments and philanthropic partners to develop technology-driven solutions to information sharing needs that respect applicable privacy, security and data integrity requirements. He does so in a way that is informed by experience and well thought out approaches that we consider an exemplar for tech firms, enterprises and government data strategists. In this OODAcast we examine some of his approaches.

Dr. Melissa Flagg of the Center for Security and Emerging Technology: Dr. Melissa Flagg is a Senior Fellow at the Center for Security and Emerging Technology (CSET) at Georgetown University. Previously she served as the Deputy Assistant Secretary of Defense for Research, responsible for policy and oversight of Defense Department science and technology programs including basic research through advanced technology development and the DoD laboratory enterprise. She has worked at the State Department, the Office of Naval Research, the Office of the Secretary of Defense for Research and Engineering, the John D. and Catherine T. MacArthur Foundation, and the Army Research Laboratory.

Dan Gerstein of RAND Corporation: Dr. Daniel Gerstein is a national security professional who has served as a senior government civilian, in uniform, in industry, in think tanks and in academia. As a senior government civilian, he served in the Department of Homeland Security as Under Secretary (Acting) and Deputy Under Secretary in the Science and Technology Directorate where he directed the organization’s over $1 billion annual budget. Dan is also the author of the recently released book entitled “The Story of Technology”.

The Big Thinkers, Authors and Analysts

Marc Ambinder of USC Annenberg School For Communication and Journalism: Marc Ambinder is a journalist, researcher, historian, author of bestselling books and a teacher/mentor to many. We invited him on the OODAcast to help our community as we continue to look for insights that can drive operational decisions.

Expert Practitioner of Analysis Carmen Medina: Carmen Medina served 32 years in senior positions at the Central Intelligence Agency, most of which focused on one of the hardest tasks in the community, that of analysis. Carmen rose to lead the strategic assessments group for the agency, then was deputy director of intelligence, the most senior leadership position for analysis at the agency and one of the most senior positions in the entire intelligence community. She also spent time as the director of the Center for the Study of Intelligence, where she oversaw ways to teach, mentor and improve analysis for the community.

John Robb on Global Guerrillas and Frameworks to Drive Decision Making: There is hardly a person more suited to speak with the OODA team on OODA Loops that former Air Force pilot John Robb. John has worked successfully in a variety of domains to include the special operations community, as an industry analyst, successful start-up founder, and national security expert.

Brad Meltzer, Bestselling Novelist With Insights To Inform Your Business Strategy: Brad Meltzer is the #1 New York Times bestselling author of The Culper Ring Trilogy (The Inner Circle, The Fifth Assassin, The President’s Shadow), The Escape Artist, The Book of Lies and many other thrillers loved by millions for their realism and well researched fact based themes and drama filled plots. He is also widely known for his non-fiction history including The First Conspiracy, a work based on extensive research that reads like a thriller while giving the foundational stories of the nation’s espionage and counterintelligence services. His most recent non-fiction book examines a plot to kill Abraham Lincoln while he was on his way to his inauguration. This one too reads like a thriller, exposing us to the realities of an era when the nation was divided by polarizing political factions.

Chet Richards on John Boyd and applying OODA principles to the business world: Chet Richards was a close associate of the late US Air Force Colonel John Boyd. He was there as the concept of the OODA Loop was being developed and constructed the first graphics of the OODA Loop from sketches Boyd drew. Chet is the author of the widely read business book “Certain to Win” which was the first book to describe Boyd’s strategy in terms familiar to business leaders and show how the OODA Loop and associated Boyd concepts apply to today’s business problems.

Michael Kanaan, Author of T-Minus AI Discusses Artificial Intelligence and Global Power: Michael Kanaan has helped a wide swath of decision-makers better grasp the nature of AI. He has a knack for expressing complex topics in clear, accurate and succinct ways and many of us in the national security community have already had the pleasure of hearing from him in person or in conferences.

Gary Harrington on Leadership Lessons from Delta Force to the CIA: Gary Harrington had a distinguished career of national service that included over three decades in top tier special operations groups including Delta Force and then transitioning into the CIA. Gary was one of the first to deploy into Afghanistan after 9/11 and was at the tip of the spear in many locations including as a solo operator in high risk venues like Yemen. Today Gary advises private clients on approaches to maintaining security and safety in a volatile and unpredictable world.

David Bray of the Atlantic Council Geotech Center: Dr. David Bray of the Atlantic Council’s Geotech Center for a wide ranging discussion on risks and opportunities in the current business environment. Decision-makers and analysts seeking insights into the future of work, the future of data, the future of trust and health will find Dr. Bray’s experiences, insights and his own continuous learning from a strong network of global thought leaders to be both informative and actionable.


Bob Gourley

Bob Gourley

Bob Gourley is the co-founder and Chief Technology Officer (CTO) of OODA LLC, the technology research and advisory firm with a focus on artificial intelligence and cybersecurity which publishes Bob is the co-host of the popular podcast The OODAcast. Bob has been an advisor to dozens of successful high tech startups and has conducted enterprise cybersecurity assessments for businesses in multiple sectors of the economy. He was a career Naval Intelligence Officer and is the former CTO of the Defense Intelligence Agency.