200 Episodes of Reimagining Cyber: Then, Now, and What’s Next

In this milestone 200th episode of Reimagining Cyber, hosts Rob Aragao and Tyler Moffitt reflect on the journey so far—exploring how cybersecurity has evolved over the past five years and where it’s headed next.

From the early focus on cyber resilience to today’s rapidly shifting threat landscape, they break down the biggest changes shaping the industry: the rise of ransomware as a business model, the growing impact of supply chain attacks, and why identity has become the new perimeter. They also debate a key question—are attackers getting more sophisticated, or just better at scaling what already works?

The conversation dives into the real-world impact of AI on both defenders and attackers, separating hype from reality, and examining how automation, tool overload, and complexity are affecting security teams. Rob and Tyler also tackle persistent challenges like phishing, human risk, and why even after decades of awareness training, the fundamentals still matter.

Looking ahead, they share candid perspectives on what organizations are getting wrong, where security investments should shift, and why prevention, prediction, and business alignment are more critical than ever. Plus, insights into the evolving role of the CISO as a true business leader.

Whether you’ve been listening since episode one or are just joining, this episode offers a thoughtful, no-nonsense look at the past, present, and future of cybersecurity.

As featured on Million Podcasts' 

Best 100 Cybersecurity Podcasts  

Top 50 Chief Information Security Officer CISO Podcasts 

Top 70 Security Hacking Podcasts

This list is the most comprehensive ranking of Cyber Security Podcasts online and we are honoured to feature amongst the best!

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Get in touch via reimaginingcyber@gmail.com