Adam Shostack is widely known in the cybersecurity world for his pioneering work on disclosing and discussing computer vulnerabilities (the CVE  (common vulnerabilities and exposures) list). He also helped formalize and train leading approaches to threat modeling and wrote the foundational book on the subject (Threat Modeling: Designing for Security).

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

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

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

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

For more see:

Adam Shostack on LinkedIn

Threats: What Every Engineer Should Learn from Star Wars

Threat Modeling: Designing for Security

Sebastian Mallaby joined the OODAcast for a discussion about the Power Law in venture capital and the rise of the global hedge fund and private equity industries.

Sebastian’s book “The Power Law: Venture Capital and the Making of the New Future” is one of the most insightful books on the venture capital industry I’ve read to date and was included in my Top 10 Security, Technology & Business books of 2022.

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

Official Bio:

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

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

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

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

Sebastian on Twitter

Book Recommendation:
The Creativity Code

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

This OODAcast features a fascinating conversation with Michael Gibson, the author of the book "Paper Belt on Fire" who is also the co-founder of the Thiel Fellowship program and the 1517 Fund, both of which focus on identifying unconventional ideas and individuals that can drive disruptive innovation in technology, arts, and science.

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

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

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

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

Additional Resources:

• Paper Belt on Fire book
• Thiel Fellowship program
• 1517 Fund

Recommended Books:

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

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

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

In the OODAcast we discuss:

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

Podcast Version:

Official Bio:

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

Recommended Books:

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

A Night to Remember

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

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

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

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

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

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

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

Additional Information:

Connect with Jen on LinkedIn

OODA Network Interview with Jen

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

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

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

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

Official Bio:

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

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

External Links:

Cult of the Dead Cow book

Joseph Menn on Twitter

Book Recommendation:  The Dawn of Everything

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

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

Discussion topics include:

- How to explain the world of quantum effects to non technical leaders and what business leaders should know about the strange world of quantum physics.

- The overall state of quantum computing today

- How non-experts can know if a claim in a quantum computing project is valid or not.

- A useful description of quantum sensing.

- The importance of quantum security.

- New NIST algorithms for improving quantum security.

- The state of quantum R&D - what comes next in the quantum industry.

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

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

Related Reading:

Explore OODA Research and Analysis

Use OODA Loop to improve your decision making in any competitive endeavor. Explore OODA Loop

Decision Intelligence

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

Disruptive/Exponential Technology

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

Security and Resiliency

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

Community

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

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.

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

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

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

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

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

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

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

Additional Resources:

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

Recommended Book:

Raven Rock by Garrett Graff