Hacking Then and Now: Ed Skoudis on AI, Pen Testing, and the Future of Cybersecurity episode artwork

EPISODE · May 19, 2026 · 32 MIN

Hacking Then and Now: Ed Skoudis on AI, Pen Testing, and the Future of Cybersecurity

from Phillip Wylie Show · host Phillip Wylie

In this episode of The Phillip Wylie Show, Phillip Wylie sits down with legendary security expert Ed Skoudis to discuss his hacker origin story, the evolution of penetration testing, and how AI is transforming offensive security.Ed shares how he got started hacking on early home computers like the Commodore VIC-20 and Timex Sinclair 1000, his journey into professional penetration testing, and the early days of DEF CON and the cybersecurity industry. The conversation also dives deep into AI-assisted penetration testing, vulnerability discovery, the future of CTFs, certifications, home labs, and what aspiring hackers should focus on to succeed in today’s rapidly changing landscape.From classic hacking stories to cutting-edge AI research, this episode is packed with insights for anyone interested in ethical hacking, red teaming, and the future of cybersecurity.========================= Connect with Ed Skoudis:LinkedIn: https://www.linkedin.com/in/edskoudisWebsite: https://www.counterhack.com/SANS Holiday Hack Challenge: https://www.sans.org/cyber-ranges/holiday-hack-challenge========================= Connect with your host, Phillip Wylie: LinkedIn: https://linkedin.com/in/phillipwylieX: https://x.com/PhillipWylieInstagram: https://www.instagram.com/phillipwylie

In this episode of The Phillip Wylie Show, Phillip Wylie sits down with legendary security expert Ed Skoudis to discuss his hacker origin story, the evolution of penetration testing, and how AI is transforming offensive security.Ed shares how he got started hacking on early home computers like the Commodore VIC-20 and Timex Sinclair 1000, his journey into professional penetration testing, and the early days of DEF CON and the cybersecurity industry. The conversation also dives deep into AI-assisted penetration testing, vulnerability discovery, the future of CTFs, certifications, home labs, and what aspiring hackers should focus on to succeed in today’s rapidly changing landscape.From classic hacking stories to cutting-edge AI research, this episode is packed with insights for anyone interested in ethical hacking, red teaming, and the future of cybersecurity.========================= Connect with Ed Skoudis:LinkedIn: https://www.linkedin.com/in/edskoudisWebsite: https://www.counterhack.com/SANS Holiday Hack Challenge: https://www.sans.org/cyber-ranges/holiday-hack-challenge========================= Connect with your host, Phillip Wylie: LinkedIn: https://linkedin.com/in/phillipwylieX: https://x.com/PhillipWylieInstagram: https://www.instagram.com/phillipwylie

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Hacking Then and Now: Ed Skoudis on AI, Pen Testing, and the Future of Cybersecurity

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This episode was published on May 19, 2026.

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In this episode of The Phillip Wylie Show, Phillip Wylie sits down with legendary security expert Ed Skoudis to discuss his hacker origin story, the evolution of penetration testing, and how AI is transforming offensive security.Ed shares how he got...

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