AI Security Is Back in the 90s | Aaron Portnoy on Hacking AI, Zero Days & Breaking Into Cybersecurity

September 19, 2026 · 2m

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What if the AI powering your company is about as hackable as a 1999 web server?


That's the uncomfortable reality Aaron Portnoy — offensive security legend, co-founder of Exodus Intelligence, and Head of Research & Innovation at Mindgard — lays out in this episode of WakeUpX.


We cover:

- Why AI security mirrors the early internet era

- The "hamster wheel" of repeating security trends

- The state of AI guardrails (and why they're not enough yet)

- How to break into cybersecurity with no degree or certifications

- Why curiosity is the most dangerous skill in offensive security


Aaron has spent 20+ years at the frontier of vulnerability research — from running the Zero Day Initiative to architecting the Pwn2Own competition, building Randori's R&D (acquired by IBM), and serving as the inaugural Hacker Fellow at Dartmouth College. He's now applying that offensive lens to AI systems at Mindgard.


Full episodes: www.wakeupxpodcast.com

Connect with Aaron: aaronportnoy.com | mindgard.ai/authors/aaron-portnoy


Topics: AI security, cybersecurity career, offensive security, zero day research, AI red team, hacking, prompt injection, Pwn2Own, Mindgard, WakeUpX

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