#37 He Hacked for 1000 Days Straight: Here’s How It Landed Him a Cybersecurity Job ft. Constantinos Kaplanis

In this episode of The Hacker’s Cache, I sit down with Constantinos Kaplanis, a senior penetration tester who took an unconventional path into cybersecurity. With no prior IT experience, he grinded his way into the field—applying to 500 jobs, enduring countless rejections, and proving his skills through sheer persistence. One of his biggest accomplishments? A 1,000-day hacking streak on TryHackMe, a testament to his dedication. We break down his journey, the job-hunting struggles, and the underrated attack vectors he’s exploited in real-world pentests. If you’re trying to break into cybersecurity, this is an episode you won’t want to miss!

Connect with Constantinos Kaplanis on LinkedIn: https://www.linkedin.com/in/ckaplanis/

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Music by Karl Casey @ White Bat Audio

Attention Listeners: This content is strictly for educational purposes, emphasizing ETHICAL and LEGAL hacking only. I do not, and will NEVER, condone the act of illegally hacking into computer systems and networks for any reason. My goal is to foster cybersecurity awareness and responsible digital behavior. Please behave responsibly and adhere to legal and ethical standards in your use of this information.

Opinions are my own and may not represent the positions of my employer.