Breaking Into Cybersecurity for Free | Aaron Portnoy on CTFs, IRC & Learning Without a Degree

September 26, 2026 · 1m

CybersecurityAI & TechnologyCareer
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Aaron Portnoy learned to hack from anonymous strangers on IRC — not in a classroom. Now he's a Hacker Fellow at Dartmouth and one of the world's leading offensive security researchers.


In this episode of WakeUpX, Aaron breaks down the free, practical roadmap he'd give anyone trying to break into cybersecurity today:


- Why Capture the Flag contests are the single best starting point

- How to build real skills without a home lab or college tuition

- The role of conference talks (published free on YouTube) in self-education

- Why curiosity beats credentials every time


Whether you're a student, a career switcher, or just security-curious — this episode is your entry point.


Full episodes: www.wakeupxpodcast.com

Aaron's site: aaronportnoy.com

Mindgard: mindgard.ai


Topics: cybersecurity career, CTF, capture the flag, offensive security, free learning, hacking, infosec, Aaron Portnoy, Mindgard, Wake Up X podcast

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