When it comes to AI and cybersecurity, there is no shortage of headlines. Every week seems to bring another prediction, warning, or bold claim about what’s around the corner. Some of those stories are about truly impactful advances, but others are little more than hype. The challenge is knowing which is which – that’s where this episode of Ready. Or Not. begins.
What follows is a conversation about skepticism, critical thinking, and why understanding technology often requires looking beyond the headlines.
Watch the full episode on Readiverse.
Key Takeaways
- Not every AI or cybersecurity headline deserves equal attention.
- AI is accelerating both cyber defense and cyberattacks, making critical thinking more important than ever.
- Hackers have helped shape modern cybersecurity by exposing weaknesses others overlooked.
- Security fundamentals still matter, even as AI changes the landscape.
- Organizations need to balance urgency with skepticism as they navigate rapid technological change.
Keeping Up With AI
In this episode (S2:E2), host Nathan Macintosh sits down with investigative cybersecurity journalist and author Joseph Menn, whose reporting career has spanned everything from nation-state hacking campaigns to organized cybercrime and the evolution of hacker culture. Together, they explore an increasingly important question: How do we separate real AI cybersecurity risks from the noise surrounding them?
One of the first topics Nathan raises is the constant stream of AI headlines. With new models and predictions, it can feel like the landscape is changing every week.
For Joseph, the challenge isn’t simply keeping up with the news. It’s keeping up with the technology itself. As organizations invest heavily in AI, new capabilities are emerging faster than many businesses, regulators, and even developers can fully understand.
At the same time, competitive pressure is driving an AI arms race, with companies rushing to build bigger models and deploy new capabilities before the implications are realized.
That doesn’t mean organizations should slow down or avoid AI altogether. But it does highlight why security leaders need to look beyond the excitement and ask tougher questions. What problem is this technology solving? What risks does it introduce? And do we understand its limitations as well as its potential?
What Matters Right Now
With AI dominating the conversation, Nathan turns to a question many leaders are asking:
Joseph points to the rapid pace of AI and its growing impact on both sides of cybersecurity. New tools are helping defenders work more efficiently, while attackers are using similar capabilities to increase the speed and scale of their operations.
One example is the rise of increasingly autonomous AI agents, a theme we covered in season 2 episode 1. As these systems take on more responsibilities, they also raise important questions about oversight, accountability, and control.
My takeaway is that the biggest AI story may not be a breakthrough model or viral prediction. It’s the steady transformation of cybersecurity already happening around us.
Sneak Peek: Risk and Retaliation
After years spent covering cybercriminals, nation-state hackers, and hacktivist groups, Joseph explains why becoming a target was never his biggest concern.
What Hacker Culture Can Teach Us
Hackers are frequently portrayed as troublemakers, but Joseph argues that hacker culture is often misunderstood. Contrary to popular stereotypes, these early innovators were driven by curiosity, creativity, and a desire to make technology better.
Groups like Cult of the Dead Cow started as teenagers exploring technology and learning how systems worked. As the internet expanded, many of them evolved into advocates for security, privacy, and digital rights.
According to Joseph, they helped build the foundation of the modern cybersecurity industry. What made them valuable wasn’t just technical expertise; it was their willingness to question assumptions and challenge conventional wisdom.
In the early days of the internet, hackers were often pointing out security flaws and pushing back on exaggerated claims. Rather than accepting things at face value, they tested systems, looked for weaknesses, and examined how things actually worked.
That mindset is just as relevant today. As AI becomes a bigger part of how we work and make decisions, critical thinking is becoming more important than ever. We may be building smarter technology, but we can’t afford to stop thinking for ourselves.
How to Stay Ready
Throughout this episode, Joseph reminds us that technology doesn’t determine outcomes on its own. People do.
AI will continue to bring new opportunities, new risks, and no shortage of headlines. The organizations that thrive will be the ones asking better questions, staying curious, and challenging assumptions. In many ways, our most valuable advantage may still be human judgment.
Keep following Ready. Or Not. for more conversations that help make sense of what’s changing, what’s worth paying attention to, and how organizations can stay ready for what’s next.
FAQs
Q: Why is keeping up with AI becoming more difficult?
A: The pace of innovation is accelerating rapidly. New models, tools, and capabilities are emerging faster than organizations can fully evaluate them. As a result, many leaders are faced with making technology decisions before best practices, regulations, and security frameworks have fully caught up.
Q: What AI developments should security leaders pay close attention to?
A: Rather than focusing on speculative predictions, leaders should pay attention to developments that are changing cybersecurity today, including AI-enabled vulnerability discovery, autonomous agents, security automation, and the growing use of AI by both attackers and defenders.
Q: What does Joseph Menn mean when he says AI is “dual use”?
A: Many AI capabilities can be used for both offensive and defensive purposes. For example, AI can help security teams identify software vulnerabilities and patch them more quickly, but attackers can use similar techniques to discover and exploit those same vulnerabilities before they’re fixed.
Q: What can modern organizations learn from hacker culture?
A: Hacker culture helped shape the cybersecurity industry by encouraging curiosity, experimentation, and questioning assumptions. Many early hackers focused on exposing weaknesses so systems could be improved, a mindset that remains valuable as organizations navigate new technologies like AI.
Q: Why does critical thinking matter more than ever before?
A: AI is making it easier to generate content, automate tasks, and spread information at scale. As a result, organizations need leaders and employees who can evaluate claims, verify information, challenge assumptions, and distinguish evidence-based insights from hype or misinformation.
Q: What’s the most positive takeaway from this episode?
A: AI isn’t just creating new risks. It’s also creating powerful opportunities for defenders. Security teams are already using AI to identify vulnerabilities, automate protective measures, and improve resilience. While the threat landscape continues to evolve, organizations also have access to capabilities that were unimaginable just a few years ago.
Katherine Demacopoulos is Senior Director of Global Content Strategy and Programs at Commvault.
