Hacker in the Loop (formerly Simply Offensive)

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...

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...

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...

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...

In this episode of Simply Offensive, Phillip Wylie sits down with longtime friend, former coworker, and cybersecurity professional Darin Fredde. The conversation traces Darin's journey from computer-aided design and telecommunications to becoming a CIO, security architect, penetration tester, and AI advocate. Along the way, Darin shares lessons learned from decades in technology, how curiosity...

In this episode of Simply Offensive, Phillip Wylie sits down with longtime cybersecurity professional Jim Nitterauer to discuss his unconventional journey from environmental microbiology researcher to entrepreneur, infrastructure engineer, security leader, and CISO. Jim shares lessons learned from building one of the early web hosting companies in the Southeast, helping scale security services at...

In this episode of Simply Offensive, Phillip Wylie sits down with V, a longtime contributor to the Dallas cybersecurity community, board member for B-Sides DFW, and cybersecurity professional with experience spanning Identity and Access Management (IAM), Governance, Risk, and Compliance (GRC), third-party risk management, and security program development. Together they discuss alternative paths...

From Law Enforcement to Cyber Threat Intelligence: Andrew “GingerHacker” Crotty’s Journey into CybersecurityIn this episode of Simply Offensive, Phillip Wylie sits down with Andrew “GingerHacker” Crotty to talk about breaking into cybersecurity, building a career in cyber threat intelligence (CTI), and creating content that helps others enter the industry. Andrew shares his unconventional path...

In this episode of Simply Offensive, Phillip Wylie sits down with fellow Suzu Labs team member Steven Swift to discuss cybersecurity from a defensive and consulting perspective. Steven shares his journey from aspiring software developer to incident response specialist, consultant, and vCISO advisor working across security governance, AI, compliance, and enterprise risk management.The conversation...

In this episode of Simply Offensive, Phillip Wylie sits down with Joff Thyer to unpack how artificial intelligence is reshaping cybersecurity. From the evolution of training and conferences to the rapid acceleration of vulnerability discovery, Joff shares hard-earned insights from decades in IT and offensive security.The conversation dives into the realities behind AI hype, where automation will...