OODAcast

Informing your decisions with intelligence, analysis, and insight on technology, business, cybersecurity, and global risk issues. Brought to you by the team at OODAloop.com

Episode 124: The History and Future of Cyberwar with Matt Devost 12/17/2024

Episode 123: Forging Leadership: Admiral Studeman on Intelligence, National Security, and Proactivity 12/17/2024

Episode 122: Embracing the Future: Insights from Brandon Jones 09/13/2024

Episode 122: Embracing the Future: Insights from Brandon Jones In this episode of the OODAcast, Bob Gourley sits down with Brandon Jones, CEO of , 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 . Related Reading: Technology Convergence and Market Disruption: Rapid advancements in technology are changing market dynamics and user expectations. See: 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: 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 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: /episode/index/show/oodacast/id/33039502

Episode 121: Dr. Bilyana Lilly on Russian Information Warfare and Navigating Future Risks 09/04/2024

Episode 121: Dr. Bilyana Lilly on Russian Information Warfare and Navigating Future Risks In this OODAcast, Matt interviews Dr. Bilyana Lilly who is an expert on Russian information warfare and geo-political risk. Bilyana is also the author of the book Russian Information Warfare and the novel Digital Mindhunters. Dr. Lilly shares her fascinating origin story and how she emerged as one of the premiere experts on Russian information warfare and geopolitical dynamics. Bilyana has worked tracking international arms and weapons supply chains, conflict zones, and other geo-political dynamics in academia, the private sector, and at internationally renowned think tanks. She shares fascinating insights from her time attending a Russian military conference with top leaders, her activities tracking information warfare and influence campaigns and then the conversation shifts to current geo-political risks including the conflict in Ukraine and what we can expect by way of targeting during the upcoming US election cycle. Official Bio: Dr. Bilyana Lilly is the chair of the cyber track at the Warsaw Security Forum and an adjunct researcher at the RAND Corporation. Dr. Lilly helps clients to detect and respond to ransomware threats and information warfare activities. Bilyana led a team that developed a threat-based risk assessment framework to prioritize vulnerabilities in critical infrastructure which the U.S. Department of Homeland Security now uses in all 50 states. She is a speaker at DefCon, CyCon, Executive Women's Forum, and the author of two books and a dozen publications, translated in Russian and Chinese. Dr. Lilly has been cited in the Wall Street Journal, Foreign Policy, and ZDNet. She has been denounced by Russia’s Ministry of Foreign Affairs. Lilly has a Ph.D. from Pardee RAND Graduate School, and master’s degrees from Oxford University (distinction) in England and the Graduate Institute in Switzerland. Additional Resources: /episode/index/show/oodacast/id/32895772

Episode 120: Leadership and Innovation with Former NASA CIO and Current Executive Leader Renee Wynn 08/02/2024

Episode 120: Leadership and Innovation with Former NASA CIO and Current Executive Leader Renee Wynn In this episode of the OODAcast, Bob Gourley interviews Renee Wynn, former Chief Information Officer (CIO) of NASA. Renee Wynn’s career trajectory is a testament to the unpredictable yet rewarding nature of professional journeys. Starting with a Bachelor of Arts in Economics from a liberal arts college, Renee navigated through various roles, ultimately becoming the CIO of NASA. She emphasizes the importance of focusing on capabilities rather than specific job titles, a mindset that allowed her to seize unexpected opportunities. The Value of Liberal Arts in Technology Renee underscores the significance of her liberal arts education in her professional life. Her studies honed her writing skills, critical thinking, and ability to organize arguments—skills essential for effective communication and policy defense in public service. This foundation proved invaluable in her roles at the Environmental Protection Agency (EPA) and NASA, where she often had to articulate complex technical concepts to diverse audiences. Renee’s tenure at the EPA was marked by her passion for the agency’s mission—ensuring clean air, water, and safe land use. Her role evolved with the advent of computers, sparking her interest in how technology can enhance mission delivery. This experience laid the groundwork for her transition to NASA, where she faced the challenges of managing a vast and complex IT infrastructure supporting global and off-world operations. At NASA, Renee encountered a culture of profound dedication and love for the agency’s mission. She detailed the complexities of NASA’s operations, which include managing data from global and space-based sources. A significant part of her role involved ensuring the cybersecurity of these operations, particularly the International Space Station, where a cyber incident could have international repercussions. Renee highlights the innovative integration of art and science in NASA’s projects. For instance, the James Webb Space Telescope’s sun shields, inspired by origami, demonstrate how artistic concepts can solve engineering challenges. This convergence of disciplines not only facilitates technical advancements but also fosters creativity and out-of-the-box thinking. The conversation delves into the burgeoning space economy, where new opportunities such as space mining, in-orbit servicing, and space tourism are emerging. Renee points out the dual nature of these advancements—each new capability also presents potential risks, particularly in cybersecurity and ethical considerations. Since retiring, Renee has embraced a portfolio career, serving on corporate and advisory boards, consulting, and engaging in public speaking. Her diverse roles keep her connected to cutting-edge technology and allow her to contribute her expertise to various sectors, including marketing and nonprofit organizations. Renee Wynn’s journey from a liberal arts graduate to the CIO of NASA exemplifies the profound impact of a well-rounded education on a career in technology. Her insights into the integration of liberal arts and technical disciplines highlight the value of diverse perspectives in solving complex problems. As the space economy continues to evolve, her experiences and foresight offer valuable lessons for the future of technology and exploration. Connect with /episode/index/show/oodacast/id/32405557

Episode 119: Megan Jaffer on Leadership, Intelligence, Innovation and Iron Butterfly Media 07/19/2024

Episode 119: Megan Jaffer on Leadership, Intelligence, Innovation and Iron Butterfly Media In this episode of OODAcast, Megan Jaffer joins the conversation to discuss her journey in the intelligence community and the creation of Iron Butterfly Media Group. Megan also discusses the expansion of Iron Butterfly Media, including new podcast series and a documentary on women in intelligence. Megan shares her background, including her studies in international relations and her experiences in South Korea. She highlights the origins of the Iron Butterfly podcast, which began as a small project during COVID-19 and has grown significantly, becoming influential in both academia and intelligence agencies. The Iron Butterfly podcast aims to share stories of women in the intelligence community, documenting their contributions and leadership. Throughout the podcast, Megan has shared numerous impactful stories. For instance, Carmen Medina’s insights on leadership, emphasizing the importance of avoiding humiliation in interactions, and Maria Whitcup’s emotional recount of engaging with a murderer, highlighting the necessity of understanding even the darkest aspects of human behavior. Future Endeavors Looking ahead, Iron Butterfly Media is expanding. The team has grown, and the podcast has moved to video format. They are also launching a new podcast, “Women in the Arena,” focusing on military women. Moreover, they are in post-production for a documentary on women in the intelligence community, aiming for completion by the end of the year. Building a Supportive Community In addition to the media group, Megan has founded the Iron Butterfly Foundation. This 501c3 organization aims to provide resources and support for women to develop and execute their ideas, fostering a community of creators. Megan Jaffer’s journey is a testament to the power of determination, networking, and passion. Her work through the Iron Butterfly podcast and foundation continues to inspire and support women in the intelligence community, ensuring their stories and contributions are recognized and remembered. For more insights and to support Iron Butterfly Media,and follow them on and . Related Reading: Technology Convergence and Market Disruption: Rapid advancements in technology are changing market dynamics and user expectations. See: 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: 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 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: /episode/index/show/oodacast/id/32214947

Episode 118: Decision-Making and Deep Tech with Laura Thomas: Insights from a Former CIA Officer 05/31/2024

Episode 117: Leading Cyber Change: Allan Friedman on the Revolution of SBOM & Future Cybersecurity Initiatives 12/05/2023

Episode 117: Leading Cyber Change: Allan Friedman on the Revolution of SBOM & Future Cybersecurity Initiatives Allan Friedman is a senior strategist at CISA (the Cyber Security and Infrastructure Security Agency) where he coordinates all of their cross-sector activities on the topic of SBOM: The Software Bill of Materials. Allan is widely known as a change agent in both the public and private sector. In government he led initiatives that created positive change in major community-wide initiatives around vulnerability disclosure and vulnerability management. He also championed efforts that made dramatic improvements in the ability to reduce risk due to the proliferation of Internet of Things devices including championing ways to keep these devices patched in the field. Now at CISA his SBOM efforts have produced action across a sector that few other initiatives have. We discuss: - What executive leaders need to know about SBOM and how to explain its benefits to any non-technical executive. - How a small team can establish a vision and make change across government, industry and academia. - What new initiatives may be coming that will support needs of the security and technology communities. Related Reading: Technology Convergence and Market Disruption: Rapid advancements in technology are changing market dynamics and user expectations. See: 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: 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 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: /episode/index/show/oodacast/id/28937468

Episode 116: Joe Sullivan on Managing Complex Security Challenges 10/11/2023

Episode 116: Joe Sullivan on Managing Complex Security Challenges 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: /episode/index/show/oodacast/id/28288505

Episode 115: Joe Tranquillo on the Revolution in Biological Science 07/28/2023

Episode 114: MITRE Futurist Charles Clancy on our Quantum Enabled Future 06/16/2023

Episode 113: Mark McGrath: John Boyd Is Far More Than The OODA Loop 06/09/2023

Episode 113: Mark McGrath: John Boyd Is Far More Than The OODA Loop 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: /episode/index/show/oodacast/id/27091986

Episode 112: Serene - The Hacker Pianist Saving Cyberspace 05/08/2023

Episode 112: Serene - The Hacker Pianist Saving Cyberspace 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: Book Recommendations: /episode/index/show/oodacast/id/26775420

Episode 111: Andy Bochman on Countering Cyber Sabotage 05/05/2023

Episode 110: Spencer Ante on Creative Capital and Disruptive Innovation 04/17/2023

Episode 110: Spencer Ante on Creative Capital and Disruptive Innovation 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: Recommended Books: /episode/index/show/oodacast/id/26563197

Episode 109: Bob Zukis and the Digital Directors Network: Helping corporate boards mitigate systemic risk 03/30/2023

Episode 109: Bob Zukis and the Digital Directors Network: Helping corporate boards mitigate systemic risk 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 . 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 that will require corporate boards to designate cybersecurity experts. How the 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 (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: /episode/index/show/oodacast/id/26386980

Episode 108: Adam Shostack on Cybersecurity and What Every Engineer Should Learn From Star Wars 03/17/2023

Episode 107: Sebastian Mallaby on How Venture Capitalists and Hedge Funds Achieve Success 03/03/2023

Episode 106: Former Head of National Intelligence Council and Deputy ODNI Neil Wiley on Intelligence Analysis 02/10/2023

Episode 106: Former Head of National Intelligence Council and Deputy ODNI Neil Wiley on Intelligence Analysis 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 /episode/index/show/oodacast/id/25892238

Episode 105: Michael Gibson Wants to Light the Paper Belt on Fire 02/01/2023

Episode 105: Michael Gibson Wants to Light the Paper Belt on Fire 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: Recommended Books: /episode/index/show/oodacast/id/25803741

Episode 104: Jimmy Soni on Why PayPal Was Successful 01/06/2023

Episode 103: Jen Hoar on Corporate Intelligence and Investigations 11/14/2022

Episode 102: Joseph Menn: Observations From Two Decades Of Tech Journalism 09/30/2022

Episode 102: Joseph Menn: Observations From Two Decades Of Tech Journalism 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: Book Recommendation: /episode/index/show/oodacast/id/24543747

Episode 101: Lawrence Gasman on Assessing the Business Impact of Quantum Technologies 09/02/2022

Episode 101: Lawrence Gasman on Assessing the Business Impact of Quantum Technologies 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: For more on quantum computing, quantum sensing and quantum security see the Related Reading: Explore OODA Research and Analysis Use OODA Loop to improve your decision making in any competitive endeavor. 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. 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. 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. 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. /episode/index/show/oodacast/id/24252063

Episode 100 - Providing actionable insights for future risks and opportunities. 08/05/2022

Episode 100 - Providing actionable insights for future risks and opportunities. In 2020, we launched the 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 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 . 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 , 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 , 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. 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. 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 ). OODAcast guests have written over 30 books. We invite you to check them out in this . /episode/index/show/oodacast/id/23969139

Episode 99: David Greenberg on Decision-making in Volatile Markets 06/24/2022

Episode 99: David Greenberg on Decision-making in Volatile Markets 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: Recommended Book: /episode/index/show/oodacast/id/23528618

Episode 98: John Spencer on Connected Soldiers and the Future of Conflict 05/13/2022

Episode 97: Duyane Norman on Disrupting the CIA to Deal with Emerging Threats 04/29/2022

Episode 97: Duyane Norman on Disrupting the CIA to Deal with Emerging Threats 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: /episode/index/show/oodacast/id/22955801

Episode 96: First Federal CISO Greg Touhill on Advanced Cybersecurity by Design 04/22/2022

Episode 95: Former Tenable CEO Ron Gula Applies a Hacker Mindset to Investing, Public Awareness, and Philanthropy 04/08/2022

Episode 95: Former Tenable CEO Ron Gula Applies a Hacker Mindset to Investing, Public Awareness, and Philanthropy 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: Book recommendations: /episode/index/show/oodacast/id/22727606

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