OODAcast

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.

Burn-In is anchored in the realities we see all around us today. Artificial Intelligence is coming fast and changing the nature of many jobs, robots and automation are bringing tremendous new capabilities but also threatening humanity with loss of employment opportunities. Parenting in a world where everyone, including kids, are always connected is already changing how we raise the next generation. And citizens with employment, privacy and security concerns are already taking action to be heard and to have a voice in what happens next. P.W. Singer and his co-author August Cole have been tracking these megatrends for years and based their book on the realities of today extrapolated into the near future. They do so in a way that will help us all think through what we want of our future.

In our OODAcast discussion, we ask P.W. questions around how he thinks, how he researches, and how he observes reality. Our discussion dove deep into the many trends he has been tracking and how he used fiction to weave them all into a more comprehensive understanding of what the human impact of technology may be.

We promise no big spoilers, but plenty of actionable context you can apply to your own strategic thinking.

OODA members can purchase the Burn-In book with a 25% discount at this page:

https://800ceoread.com/OODA

Additional Reading:

https://www.oodaloop.com/archive/2019/12/02/top-10-security-technology-and-business-books-of-2019/

https://www.oodaloop.com/archive/2018/11/26/best-security-business-and-technology-books-of-2018/

https://www.oodaloop.com/ooda-original/2017/12/08/best-security-intelligence-technology-books-2017/

https://www.oodaloop.com/ooda-original/2016/12/07/best-security-business-technology-books-2016/

In this OODAcast, OODA LLC CEO Matt Devost interviews Congressman Will Hurd in 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.

Will Hurd, a San Antonio native and Texas A&M Computer Science Graduate, never planned on being a member of Congress. Congressman Hurd was excited to spend his entire career serving his country by stopping terrorists, preventing Russian spies from stealing our secrets and putting nuclear weapons proliferators out of business as an undercover officer in the CIA, until he realized that his expertise in cybersecurity and intelligence was sorely needed in Congress – the people charged with making informed decisions about how to serve and protect our country. Since being elected in 2014, Will has continued to blaze his own trail to deliver bipartisan results for the 800,000 Texans he calls his “bosses” by working with anyone – regardless of politics and party to help make sure our kids are ready for the future, that our country is safe and that the United States will always be the leader of the free world. Texas Monthly and Politico Magazine have called him “the Future of the GOP.” His efforts to put good policy over good politics have clearly struck a chord in a country that is often consumed with what divides us instead of what unites us.

Additional Resources:

Congressman Will Hurd

The Future of AI is Largely Unwritten with Will Hurd

AI Security: Four Things to Focus on Right Now

A Decision-Maker’s Guide to Artificial Intelligence

When Artificial Intelligence Goes Wrong

Artificial Intelligence for Business Advantage

The Executive’s Guide To Quantum Computing:

Is Quantum Computing Ushering in an Era of No More Secrets?

Quantum Computing Sensemaking

Mitigating Risks To America’s Cognitive Infrastructure

Cyber Sensemaking:

11 Habits of Highly Effective CISOs

Essential Management Strategies for Cybersecurity

10 Red Teaming Lessons Learned Over 20 Years

The Five Modes of HACKthink

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.

In his time at Palantir Robert has participated in several responses to crisis situations where data solutions were needed quickly in order to save lives and limit loss of property. He captured many lessons learned from past responses to crisis situations in a recent Medium post titled: In crisis response, answer the simple questions first. The lessons learned from this post is very relevant to the situation many decision-makers are wrestling with right now so we sought out time with Robert to join us on the OODAcast.

Topics we reviewed with Robert include:

• Doing business in a global corporation where most of the team are operating out of their homes
• Lessons learned from crisis response including disaster relief work globally
• Lessons learned from support to public health
• Use cases for data integration and analysis in public health, including long-term research and informing operational decisions
• Privacy in a crisis
• Speed of delivery of solutions in a crisis (how can solutions be fielded faster?)
• What is data governance and what parts are still applicable in a crisis?
• What is meant by focusing on "simple questions first"

Related Resources:

• In Crisis Response, Ask Simple Questions First: The article that inspired this discussion
• The Executive’s Guide to Quantum Computing: What business decision-makers need to know now about quantum superiority
• Context on Make vs Buy in the Federal Ecosystem: If you know of anyone anywhere in government who is thinking of building/coding a new data system to track issues around the pandemic they should just stop and should buy a commercial platform.
• OODAcast on YouTube: OODA’s YouTube Channel

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.

Topics discussed included:

• The current market for businesses that offer cybersecurity products and services
• How the old model of Product-Market fit is increasingly now one of Product-Channel-Market fit
• The approach to technology development and maintenance that investment banks, investors and acquirers need to see
• The dynamic between innovators and regulators
• The most rapid areas of innovation and investment today
• The best approaches to technology due diligence and cybersecurity due diligence

JC Raby has more than 16 years of investment banking experience in mergers and acquisitions as well as private and public financings. JC’s clients include leading Fortune 500 acquirers and middle-market growth companies across a number of industries including media and Technology (software, business services, and communications equipment) manufacturing and consumer products, together accounting for over $9 billion in transaction value.

Prior to founding Boston Meridian, JC was a senior executive for Thomas Weisel Partners (now Stifel Financial) a leading San Francisco based merchant bank in which JC ran the Boston Investment Banking Group, with responsibility to grow the firm’s relationships with leading East Coast technology firms as well as the New England private equity community. Prior to joining Thomas Weisel Partners, JC was a Vice President at Montgomery Securities (now Bank of America Securities) where he was responsible for the execution of merger and acquisition transactions; and began his career in the corporate finance group at PaineWebber Inc. (now UBS Securities).

Related Content:

• Boston Meridian Partners
• Tighten Your OODA Loop on Covid-19
• How the Coronavirus will impact your mid to long range strategic planning
• Mitigating Risks To America’s Cognitive Infrastructure
• OODA’s Special Reporting on the Federal Technology Market.
• The Top 10 Security, Technology, and Business Books
• OODAcast on YouTube: OODA’s YouTube Channel

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.

In 1999, Scott famously articulated that "You have zero privacy anyway. Get over it." and we revisit that quote in the context of today's technology and social media environment. This OODAcast with OODA CEO Matt Devost and McNealy also covers:

• McNealy's origin story including the founding of Sun
• His perspective on today's technology landscape and technology innovation
• Leadership lessons derived over the course of his career
• His view on Coronavirus
• The future of education and how it looks more like Fortnite than Zoom.

Additional References:

• Curriki site
•  McNealy is an OODA Advisory Board Member
• Tighten Your OODA Loop on Covid-19
• How the Coronavirus will impact your mid to long range strategic planning
• Mitigating Risks To America’s Cognitive Infrastructure
•  OODA’s Special Reporting on the Federal Technology Market.
• The Top 10 Security, Technology, and Business Books 
• OODAcast on YouTube: OODA’s YouTube Channel

Balan Ayyar is the Founder and CEO of Percipient.ai, 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. He is a disciplined visionary with an incredible thurst for learning and a knack for connecting with others.

We loved the fact that we recorded him while he was at his desk and when we started asking about what he is reading he could quickly grab his favorite books and give his his insights. It is also always great to talk to a real Air Force leader about the OODA Loop and the model of continuous action and how it applies to not just military ops but business.

Topics we covered included:

• How the national security establishment needs to change to get ready for the new world
• Views on the struggle between open societies and closed/dictatorship/communist societies and how that relationship is
  changing now.
• Role that AI can play to accelerate the return of our economy
• Concepts for getting classified information to users where ever they are, including at their homes. Seems technically feasible, and seems like the risk/reward equation may have shifted a bit recently.
• Ideas on how US tech firms can better support the nation in the new economy.
• Lessons learned from leadership of Percipient that could be helpful to other CEOs or other leaders in government.

Related Resources:

• Percipient.Ai
• Balan Ayyar on LinkedIn
• An Executive’s Guide to Cognitive Bias in Decision Making: How we think is critically important.
• Mitigating Risks To America’s Cognitive Infrastructure
• How the Coronavirus will impact your mid to long range strategic planning: Advice for decision-makers in the business community.
• The Executive’s Guide to Quantum Computing: What business decision-makers need to know now about quantum superiority
• OODA COVID-19 Sense-making: A dynamic resource for OODA Network members looking for Coronavirus/COVID-19 information to drive their decision-making process. We’ll update it with new links as we encounter them. This is not meant to be a comprehensive list, but rather a compilation of the most useful resources.
• Context on Make vs Buy in the Federal Ecosystem: If you know of anyone anywhere in government who is thinking of building/coding a new data system to track issues around the pandemic they should just stop and should buy a commercial platform.
• OODAcast on YouTube: OODA’s YouTube Channel

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.

She is also a writer, co-authority two books, Rebels at Work: A handbook for leading change, and Rebels at Work Dispatches.

We have been huge fans of Carmen's for years, having observed her practicing her art in and out of the intelligence community. In this wide-ranging discussion we covered many topics of high relevance to business and government leaders, including:

• Some of her recent writing on analytical thought
• Ways to estimate intentions of others even in chaotic environments
• Using the actions of leaders to track intent
• Cognitive traps, cognitive bias and analytical methods that can mitigate problems with these traps
• Human nature when it comes to analysis, and ways we can improve on our own weaknesses when it comes to thinking
• The paradox of warning
• The streetlight effect
• Her sources of information

Related Resources:

• Thinking in the Time of the Coronavirus Part One
• Thinking in the Time of the Coronavirus Part Two
• Rebels at Work: A handbook for leading change from within
• An Executive’s Guide to Cognitive Bias in Decision Making: How we think is critically important.
• A Decision-Makers’s Guide to Artificial Intelligence: A plain english overview with the insights you need to drive corporate decisions
• The Executive’s Guide to Quantum Computing: What business decision-makers need to know now about quantum superiority
• The Executive’s Guide to the Revolution in Biology: An overview of key thrusts of the transformation underway in biology and offers seven topics business leaders should consider when updating business strategy to optimize opportunity because of these changes.
• OODA COVID-19 Sense-making: A dynamic resource for OODA Network members looking for Coronavirus/COVID-19 information to drive their decision-making process. We’ll update it with new links as we encounter them. This is not meant to be a comprehensive list, but rather a compilation of the most useful resources.
• The 2020 OODA Cybersecurity Watch List: list can serve multiple stakeholders. Investors can find firms that have demonstrated good product-market fit and are good candidates for follow-on funding. CISOs can find companies that have demonstrated real disruptive technology potential and at least enough traction to prove they are worth considering.
• OODAcast on YouTube: OODA's YouTube Channel

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 Malvertisements.com, the first and only public database documenting malvertising incidents on a continuous basis. Prior to RiskIQ, Elias was VP of R&D at Securant Technologies (acquired by RSA), which pioneered identity and access management for web applications. At Securant, he was instrumental in creating now-commonplace technologies for single sign-on (SSO) security.

In this wide ranging discussion Matt Devost and Bob Gourley discussed several topics of interest to the community, including:

• Lou's leadership style and lessons learned relevant to leaders of other firms in the cybersecurity domain
• The Anti-Malvertising working group and Lou's leadership there
• Views on the dynamic cyber threat
• Ways the threat has been changing because of the pandemic and RiskIQ's response to that
• RiskIQ's transition to remote ops
• The future of cybersecurity

Related Resources:

• RiskIQ
• RiskIQ Daily Cybercrime Update
• 10 Red Teaming Lessons Learned Over 20 Years – Red teaming is one of the most valuable things you can do within your organization.  OODA CEO and Co-Founder Matt Devost offers up his top ten red teaming lessons learned from over two decades of red teaming across hundreds of engagements.
• OODA’s Special Reporting on the Federal Technology Market: This market should be part of any tech firm's strategy
• OODA Special Report on Best Practices for Agile Cybersecurity Tips from our experts
• Context on Make vs Buy in the Federal Ecosystem: If you know of anyone anywhere in government who is thinking of building/coding a new data system to track issues around the pandemic they should just stop and should buy a commercial platform.
• OODAcast on YouTube: OODA’s YouTube Channel

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.

In this wide ranging discussion we asked Cameron questions including:

• How she started in cybersecurity and privacy (it was an internship with DISA)
• Perspectives on how cybersecurity professionals should continue to learn
• Seeking balance between education, training, certifications and experience in the cybersecurity field
• Lessons she has learned in her career regarding best practices
• Observations on adversary innovations
• How to help organizations seeking tailored solutions in security that work for them
• The most important message for boards of directors and CEOs regarding cybersecurity
• Considerations regarding ROI in cybersecurity
• Ways to accelerate the development of a cybersecurity team
• The importance of trust in the relationship between a client and cybersecurity team

Related Resources:

• Cross Country Consulting
• Cameron Over on LinkedIn
• 10 Red Teaming Lessons Learned Over 20 Years – Red teaming is one of the most valuable things you can do within your organization.  OODA CEO and Co-Founder Matt Devost offers up his top ten red teaming lessons learned from over two decades of red teaming across hundreds of engagements.
• OODA’s Special Reporting on the Federal Technology Market: This market should be part of any tech firm's strategy
• OODA Special Report on Best Practices for Agile Cybersecurity Tips from our experts
• Context on Make vs Buy in the Federal Ecosystem: If you know of anyone anywhere in government who is thinking of building/coding a new data system to track issues around the pandemic they should just stop and should buy a commercial platform.
• OODAcast on YouTube: OODA’s YouTube Channel

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.

Topics discussed include: 

• The challenges Phil faced at DHS, including the need to lead change across a broad stakeholder community.
• The nature of the work at GCA
• What executives need to know about DNS and DMARC
• Ways people can get involved with the GCA
• How the GCA moved into action as the world shifted to WFH
• The future of cybersecurity

Related Resources:

• The Global Cyber Alliance
• Phil Reitinger on LinkedIn
• 10 Red Teaming Lessons Learned Over 20 Years – Red teaming is one of the most valuable things you can do within your organization.  OODA CEO and Co-Founder Matt Devost offers up his top ten red teaming lessons learned from over two decades of red teaming across hundreds of engagements.
• OODA’s Special Reporting on the Federal Technology Market: This market should be part of any tech firm's strategy
• OODA Special Report on Best Practices for Agile Cybersecurity Tips from our experts
• Context on Make vs Buy in the Federal Ecosystem: If you know of anyone anywhere in government who is thinking of building/coding a new data system to track issues around the pandemic they should just stop and should buy a commercial platform.
• OODAcast on YouTube: OODA’s YouTube Channel