HeyJaredSimply Offensive
Phillip Wylie interviews cybersecurity industry experts on offensive security and techniques around penetration testing and red teaming.
- Indexed episodes, last 90 days
- 4
- Latest publication
- Aug 25, 2026
- Audience
- Checking…
- Earliest in this view
- Jul 7, 2026
Latest episodes
Building an Agentic Hacking Harness with Jacob Krell (opens the original)
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What happens when AI moves beyond answering pentesting questions and starts actively participating in the testing workflow? In this episode of Hacker in the Loop , Phillip Wylie is joined by his colleague Jacob Krell for a hands-on look at building an agentic hacking harness using Cursor, Metasploit, MCPs, AI models, and custom guardrails . Jacob walks through the process in real time, showing how an AI-powered environment can research techniques, build tools, maintain engagement state, execute
Inside DEF CON's IoT Village with Rachael Tubbs, PhD (opens the original)
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What does it take to build one of DEF CON's largest and most popular villages?In this episode of Simply Offensive, Phillip Wylie sits down with Rachael Tubbs, PhD, Research Director at Independent Security Evaluators (ISE) and one of the leaders behind IoT Village, to discuss the evolution of one of the cybersecurity community's favorite DEF CON attractions.From Bluetooth-enabled toilet seats and connected litter boxes to IoT security research, hacker psychology, and advice for first-time DEF CO
AI Won't Make You a Hacker: Why Fundamentals Still Matter (opens the original)
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Artificial intelligence is transforming offensive security, but does that mean traditional penetration testing skills are becoming obsolete? In this episode of Simply Offensive, Phillip Wylie is joined by offensive security researcher Milton "wetw0rk" Valencia and Suzu Labs offensive security practitioner Jacob Krell for an in-depth discussion about the future of penetration testing, exploit development, and the role AI is playing in modern offensive security. Drawing from decades of combined ex
AI, Certifications, and Security Reality with Katherine McNamara (opens the original)
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In this episode of Simply Offensive, Phillip Wylie welcomes Katherine (Kat) McNamara, Technical Solutions Architect at Cisco and holder of two prestigious Cisco Certified Internetwork Expert (CCIE) certifications. Kat shares her remarkable journey from overcoming significant personal challenges to becoming one of the industry's leading networking and security professionals.The conversation explores the evolution of cybersecurity careers, the value of certifications versus degrees, today's hiring
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