From Analog Hacks to Agentic AI – Denis Calderone on the Evolution of Offensive Security

In this episode of Simply Offensive, host Phillip Wylie sits down with Denis Calderone, Co-Founder and Principal at Suzu Labs, to discuss his journey from early curiosity about how technology works to building a long career in cybersecurity consulting and penetration testing.Denis shares stories from the early days of security when breaches often went unnoticed, how compliance shaped the industry, and how today’s AI-driven development is creating both opportunity and risk. The conversation explores the evolution of pentesting, the importance of community in hiring, the growing role of AI in offensive security, and why human expertise still matters despite increasing automation.The discussion also highlights dark web monitoring, talent development, and how relationships—not transactions—drive long-term cybersecurity success.

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Connect with Denis Calderone

LinkedIn: https://www.linkedin.com/in/deniscalderone/

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Connect with your host, Phillip Wylie:

LinkedIn: https://linkedin.com/in/phillipwylie

X: https://x.com/PhillipWylie

Instagram: https://www.instagram.com/phillipwylie

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Presented by Suzu Labs

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All the ways to connect with @Suzulabs

https://suzulabs.com

https://x.com/suzulabs

/ suzu-labs

Chapters00:00 Introduction to Cybersecurity Journeys03:17 From Network Technician to Cybersecurity Professional05:52 The Importance of Experience in Cybersecurity09:04 Adopting a Purple Team Mindset11:45 The Role of Tabletop Exercises in Security Training14:24 Understanding Learning Styles in Cybersecurity Training17:03 The Impact of AI on Cybersecurity Operations19:47 Challenges in Corporate Security Mindsets22:34 The Future of Cybersecurity Training25:09 Connecting with the Cybersecurity Community29:03 Simply Offensive Outro