#13 Hacking Time: Real World Skills They Don't Teach You | Trent Darrow

The Hacker's Cache

Kyser Clark interviews Trent Darrow, a senior penetration tester and cyber protection team crew lead. They discuss Trent's background, certifications, and his role in building a red team. They also touch on ethical dilemmas in the industry, the effectiveness of certifications in preparing for real-world pen testing, and the importance of skills like time management and effective communication. In this conversation, Trent and Kyser discuss time management in cybersecurity exams, the challenges of scanning large networks, the role of a cyber warfare technician, the transition between civilian and military careers, strategies for preparing for the OSCP and OSEP exams, the value of participating in CTFs, and the future of the cybersecurity field.
Connect with Trent Darrow on LinkedIn: https://www.linkedin.com/in/trenton-darrow/

Takeaways:
Trent's background spans help desk, IT specialist roles, network engineering, and cybersecurity contracting, with certifications like OSCP, GCFA, GWAPT, GPEN, and GCPN.
Real-world skills like time management, note-taking, and communication are crucial, differing from those needed for exams or CTFs.
Ethical dilemmas, such as downgrading findings to please clients, can be common in the industry.
Preparing for certifications like OSCP and OSEP requires practice, extensive note-taking, and ensuring tools work properly through a proxy.
AI isn't a threat to cybersecurity jobs, but learning web application security is essential for staying competitive.

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Music by Karl Casey @ White Bat Audio
Attention viewers/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.
The postings on this site are my own and may not represent the positions of my employer.

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1. Introductions (00:00:00)

2. Rapid Fire Questions (00:06:16)

3. Ethical Dilemmas in Pentesting (00:08:40)

4. Real-World vs. Exam Time Management (00:17:09)

5. Preparing for OSCP and OSEP Certifications (00:27:15)

6. Burnout & AI (00:37:08)