100 Episodes of OODAcast: Providing actionable insights for future risks and opportunities.

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.

Podcast Version:



The following is a full list of OODAcast episodes:


David Greenberg on Decision-making in Volatile Markets

John Spencer on Connected Soldiers and the Future of Conflict

Duyane Norman on Disrupting the CIA to Deal with Emerging Threats

First Federal CISO Greg Touhill on Advanced Cybersecurity by Design

Former Tenable CEO Ron Gula Applies a Hacker Mindset to Investing, Public Awareness, and Philanthropy

Jim Lawler on the Art of Espionage and the Perfect Intelligence Operation

Lifelong Hacker and Experienced Security Executive Alyssa Miller, Author of Cybersecurity Career Guide

Dr. Scott Shumate Profiles Russian President Vladimir Putin

Chris Butler on the Value of Adversarial Thinking in Product Design and Management

Charity Wright on China’s Digital Colonialism

Jan Chipchase on Field Research for Actionable Insights

Ben Dubow on Detecting and Countering Malign Influence Operations

Jahon Jamali On Bitcoin, Ethereum, and the Coming Metaverse

Maury Rogow: Every Corporation Will Have A Metaverse Strategy

Alan Cohen of DCVC on Investing in Deep Tech For Humanity

Digital Self Sovereignty and Avoiding the Long Night with John Robb

Inman’s Rules: The Enduring Principles of Operational Intelligence

The Man Who Protects Our Secrets: Bob Bigman on Mitigating Enterprise Risks

Randall Fort on The Future of the Metaverse And Its Cybersecurity and Intelligence Implications

Amr Awadallah On The Biggest Challenges And Opportunities in Enterprise IT Today

Sir David Omand on Leveraging How Spies Think In Our Business and Personal Lives

Jessica Gulick: An accomplished cybersecurity practitioner turned CEO on future focused leadership

Lance Mortlock On Scenario Planning to Drive Strategic Decisions

Jer Thorp on Living in Data and Creating Better Futures

Tony Tether On Technology Leadership and Lessons Learned From DARPA

Cofer Black on Leadership Lessons Learned and Speaking Truth to Power

Gaurav Banga On Mitigating Cyber Threats Through Deep Insight Into Things That Matter Most

Kim Zetter on Understanding the Realities of Cyberthreats and How Code Has a Story to Tell

Junaid Islam on Zero Trust Architecture

Scythe CEO Bryson Bort on Enhancing Security with Realistic Adversary Emulation

Trond Undheim on the Future of Technology and a Framework for Analyzing Forces of Disruption

Jeremy King on the greatest leaders he has ever seen (and how we can all keep learning leadership)

Ben Ford, Founder of Commando Development, on the OODA Loop and Tech Leadership

Matt Devost on Entrepreneurship, Innovation, and Succeeding in Competitive Environments

Max de Groen of Bain Capital PE on the Megatrends Driving Future Tech Enabled Investments

Jim Clapper Shares Wisdom From A Career in Operational Intelligence

Ray Wang, CEO and Founder of Constellation Research, On The Business Impact of Technology

Lisa Porter On Innovation, Technology, Security and Lessons in Leadership

Nate Fick on Dynamic Leadership and Adapting to Change

Lessons In Leadership, Intelligence Analysis, and Geopolitical Trends From Retired LTG Robert Ashley, former Director of DIA

Lessons In Leadership From Ellen McCarthy and Her Journey From Junior Analyst To The Most Senior Echelons of the Intelligence Community

Robert Wallace on a Career in Intelligence and The Spy Sites Series and Spy Craft

Blake Bartlett, CEO of Janes, On Leadership and Decision Making In The Modern Age

Michele Wucker on Identifying and Confronting the Obvious Risks of Gray Rhinos

Vikram Sharma, CEO of Quintessence Labs on Leadership in the Quantum Era

Former CIA Officer Rob Richer on the Geopolitical Landscape, Leadership Lessons Learned, and Supporting Decision-makers

Camila Russo on Ethereum and the Future of Decentralized Finance (DeFi)

Will Hurd on Skills For Success In The Modern Age

Kathy and Randy Pherson, Authors of Critical Thinking for Strategic Intelligence

Ric Prado on Intelligence Operations and a Legendary Career in the CIA

Matt Devost Provides Context on the Top 10 Security, Technology, and Business Books of 2020

Mischel Kwon, Founder and CEO of W@tchTower

Masha Sedova, Co-Founder Elevate Security on Human Risk Management

Bob Gourley on Operational Intelligence for Strategic Decision-making

CEO of Women’s Society of Cyberjutsu and Cybersecurity Leader Mari Galloway

Paul Kurtz, Iconic Cybersecurity Leader and Founder of TruSTAR

Rear Admiral Paul Becker, USN (ret) on leadership in the modern age

Dr. Melissa Flagg of the Center for Security and Emerging Technology

Mark Weatherford On Leading Change As a CISO

Matt Devost on Hacking Entrepreneurship and Identifying Threats and Opportunities

Kevin Roberts on Leadership, Decision-making, and Focused Action

Gary Harrington on Leadership Lessons from Delta Force to the CIA

Michael Kanaan, Author of T-Minus AI Discusses Artificial Intelligence and Global Power

Jim Miller on Managing Policy in an Age of Constant Disruption and Dynamic Threats

Chet Richards on John Boyd and applying OODA principles to the business world

Courtney Bowman, Privacy and Civil Liberties Engineer, Palantir Technologies

Kevin DeSanto On Due Diligence and M&A Transactions and Trust Based Networking

Bradley Rotter On The Future Of Work, CryptoCurrencies, Quantum Computing and Leadership

Andy Lustig On Legal and Due Diligence Support In The High Tech Era

Paul Pagnato, CEO and Founder at PagnatoKarp and Author of The Transparency Wave

Alsop-Louie Partner and Famed Tech Executive Bill Crowell on Technology Due Diligence

Brad Meltzer, Bestselling Novelist With Insights To Inform Your Business Strategy

John Robb on Global Guerrillas and Frameworks to Drive Decision Making

Bobbie Stempfley of Carnegie Mellon University Software Engineering Institute

A Conversation With Marc Ambinder of USC Annenberg School For Communication and Journalism

A Conversation with Peter Singer on Useful Fiction and the book Burn-In

Congressman Will Hurd on the future of technology and policy

Robert Fink of Palantir on Lessons Learned From Using Data In Crisis Response

JC Raby of Boston Meridian Partners

Renowned Business Executive Scott McNealy, Co-Founder of Sun Microsystems

CEO of Percipient Balan Ayyar on the business of AI

Expert Practitioner of Analysis Carmen Medina

Lou Manousos, CEO of RiskIQ

Operational Cybersecurity Leader Cameron Over

Cybersecurity Icon Phil Reitinger, CEO of the Global Cyber Alliance

Seasoned Industry Executive and Serial Entrepreneur Henry Harrison, CTO of Garrison

Quantum Security Practitioner Jane Melia of QuintessenceLabs

Former CIA CTO Bob Flores

Tony Cole of Attivo Networks

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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.