In this OODAcast episode, host Matt Devost sits down with Maxie Reynolds, author of The Art of the Attack, to explore the evolution of her unique career from offshore oil rigs to elite red teaming and cybersecurity innovation. Maxie shares how her unconventional path, working a decade in oil and gas, earning degrees while on remote rigs, and eventually breaking into cybersecurity at PwC, shaped her approach to physical and digital security. Her journey led to the creation of a company that builds underwater data centers, a novel fusion of her industrial and red teaming experiences. She discusses the rising interest in submerged infrastructure, particularly after China's moves in the space and the demands of modern AI-driven cooling systems.

The conversation dives deep into what it means to adopt an "attacker mindset", seeing opportunities where others see obstacles and using architecture, human psychology, and environment as vectors for access. Maxi outlines how her social engineering engagements hinge on understanding perception, psychology, and pretext creation rather than just technical exploits. She offers real-world stories of infiltrating secure facilities and engaging high-stakes targets using layered personas and misdirection. Through it all, she emphasizes the role of self-awareness, stress management, and emotional discipline in high-pressure operations, often drawing parallels between red teaming and stoicism.

Maxie and Matt also examine how to responsibly deliver red team results to leadership, balancing candor with empathy to ensure organizations grow stronger without shame or defensiveness. They reflect on the future of AI in security, the persistence of physical threats, and the irreplaceable value of human judgment. The episode wraps with a powerful reading list and a shared love of books, highlighting titles that explore geopolitics, materials science, and the ungoverned world of the open ocean. This episode is packed with insight, storytelling, and practical wisdom for cybersecurity professionals, technologists, and leaders looking to understand how adversaries think—and how to outsmart them.

Additional Links:

The Art of Attack: Attacker Mindset for Security Professionals by Maxie Reynolds

Maxie on Twitter/X

Book Recommendations:

How the World Really Works: The Science Behind How We Got Here and Where We're Going by Vaclav Smil

The Outlaw Ocean: Journeys Across the Last Untamed Frontier by Ian Urbina

Prisoners of Geography: Ten Maps That Explain Everything About the World by Tim Marshall

Chip War: The Fight for the World's Most Critical Technology by Chris Miller

Stuff Matters: Exploring the Marvelous Materials That Shape Our Man-Made World by Mark Miodownik

In this episode of the OODAcast, host Matt Devost is joined by Alok Sama, author of The Money Trap, for a compelling conversation about Sama’s journey from modest beginnings in India to leading some of the most ambitious investment efforts in tech history. Sama recounts his early days in Delhi, the unlikely path to Wharton, and his time at Morgan Stanley before stepping into the eye of the storm as President and CFO of SoftBank. Alongside Masayoshi Son, he helped deploy the groundbreaking Vision Fund, a $100B initiative that forever changed the scale of tech investing. Sama offers behind-the-scenes insights into the wild ride of investing in giants like Uber, WeWork, and ARM, reflecting on how bold vision and massive capital shaped, and sometimes distorted, the future of technology.

es candid lessons from massive wins and public missteps, including the now-infamous WeWork saga. He also delves into how a high-stakes smear campaign impacted his health and priorities, offering an unflinching look at the personal costs of operating at the top of global finance. Throughout the episode, Sama’s honesty, humor, and humility shine, echoing the voice that made his book so impactful.

Beyond business, the conversation turns deeply personal. Sama reflects on what really matters after decades of chasing financial success. He opens up about regrets around time lost with loved ones, the role of humility in leadership, and how ancient Indian philosophy helped him reframe his priorities. Now entering a new chapter focused on writing, mentoring, and giving back, Sama offers timeless advice for entrepreneurs, investors, and anyone navigating high-pressure careers. This episode is a must-watch for those curious about the intersection of power, capital, and purpose.

Additional Links: Alok on X

Book Recommendation: The Rings of Saturn by W.G. Sebald

In this OODAcast, Chris Wysopal shares his insights from decades in cybersecurity, detailing his journey from the early hacking collective "The L0pht" to co-founding Veracode. Wysopal reflects on the evolution of cybersecurity, highlighting his early contributions to vulnerability research and advocating the importance of adversarial thinking in security practices. He emphasizes the transition from traditional vulnerability testing to comprehensive application risk management, recognizing the increased reliance on third-party software and the escalating complexity of securing modern applications.

Wysopal also discusses how generative AI technologies are significantly accelerating application development but simultaneously creating substantial security challenges. He stresses that while AI-generated applications multiply rapidly, their vulnerability density remains comparable to human-written code. To manage this growing risk, Wysopal underlines the necessity of integrating automated, AI-driven vulnerability remediation into the software development lifecycle.

Looking forward, Wysopal advocates for embedding security deeply within the application creation process, anticipating that AI will eventually assist in producing inherently secure software. However, he also underscores the enduring threat of social engineering attacks, urging enterprises to prioritize comprehensive security awareness programs to bolster their overall cybersecurity posture and resilience.

The conversation examines some very interesting correlations between the mindset of the great hackers and the success of great entrepreneurs. Both take a good bit of grit, an ability to focus and be creative and perhaps most importantly: Persistence.

Learn more about Chris Wysopal's approaches and the company he founded at Veracode. For insights into reducing your organization's attack surface see: State of Software Security 2025