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Ed Williams, Vice President of EMEA Consulting and Professional Services (CPS) at TrustWave, shares his two decades of pentesting and red teaming experience with Cyber Work listeners.

From building his first programs on a BBC Micro (an early PC underwritten by the BBC network in England to promote computer literacy) to co-authoring award-winning red team security tools, Ed discusses his favorite red team social engineering trick (hint: it involves fire extinguishers!), and the ways that pentesting and red team methodologies have (and have not) changed in 20 years. As a bonus, Ed explains how he created a red team tool that gained accolades from the community in 2013, and how building your own tools can help you create your personal calling card in the Cybersecurity industry!

Whether you're breaking into cybersecurity or looking to level up your pentesting skills, Ed's practical advice and red team “war stories,” as well as his philosophy of continuous learning that he calls “Stacking Days,” bring practical and powerful techniques to your study of Cybersecurity.

0:00 - Intro to today's episode
2:17 - Meet Ed Williams and his BBC Micro origins
5:16 - Evolution of pentesting since 2008
12:50 - Creating the RedSnarf tool in 2013
17:18 - Advice for aspiring pentesters in 2025
19:59 - Building community and finding collaborators
22:28 - Red teaming vs pentesting strategies
24:19 - Red teaming, social engineering, and fire extinguishers
27:07 - Early career obsession and focus
29:41 - Essential skills: Python and command-line mastery
31:30 - Best career advice: "Stacking Days"
32:12 - About TrustWave and connecting with Ed

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Build your own pentesting tools and master red teaming tactics | Ed Williams