In Episode 12 of Hack Dissection, Mike Lisi sits down with longtime friend and respected security educator Phillip Wylie — Chief Security Evangelist and Senior Consultant at Suzu Labs, and host of the Simply Offensive and The Phillip Wylie Show podcasts. Together, they look back on their early days pursuing the OSCP, discuss how offensive security has evolved over the last decade, and break down the changing realities of penetration testing in today’s environment.

Phillip shares stories from the field, including a memorable web app penetration test involving SQL injection, weak credential practices, and the all-too-common misuse of risk acceptance. The conversation also explores the growing importance of web app testing, IoT attack paths, continuous remediation, and why foundational skills like networking, operating systems, and scripting still matter for anyone serious about building a career in cybersecurity.

They also dig into mentorship, community involvement, conference speaking, and the future of the industry — from AI as a force multiplier to the value of staying adaptable in a field that never stops changing. Whether you’re an experienced practitioner or just breaking into offensive security, this episode is packed with practical insight, career wisdom, and real-world perspective from one of the community’s most generous voices.