The OSCP Won’t Save You ft. Tyler Ramsbey #36

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Many aspiring penetration testers believe that earning the OSCP is the ultimate proof of their skills—but what happens when they step into a real-world engagement? In this episode of The Hacker’s Cache, Tyler Ramsbey joins me to break down the hard truth about OSCP, the gaps it leaves in real-world pentesting, and why experience always outweighs certifications. We discuss rookie mistakes, the reality of internal assessments, and why leadership and communication skills are just as critical as technical expertise. Whether you're chasing the OSCP or already have it, this episode will challenge what you think you know about offensive security.

Connect with Tyler Rambey on LinkedIn:   / tyler-ramsbey-86221643  

Subscribe to Tyler Ramsbey on YouTube:    / @tylerramsbey  



Check out the Hack Smarter Community: https://hacksmarter.org/

As a cybersecurity professional with over six years of experience, I focus on strengthening digital assets against ever-changing cyber threats. I specialize in penetration testing, ethical hacking, red teaming, and offensive security. I excel at uncovering and addressing vulnerabilities in networks and web applications.

My mission is to make cyberspace better & safer for everyone by committing to lifelong learning, sharing knowledge with the community, and inspiring others to do the same.

Credentials:

• BS in Cybersecurity Management and Policy from UMGC.

• 16 certifications including OSCP, OSWA, CISSP, PWPA, eJPT, OSWP, CASP+, PenTest+, CEH, CySA+, CCNA, Cyber Ops-A, Cloud+, Linux+, Security+, and Network+.

• Pwned 109 HTB machines and mastered 218 THM rooms, securing top leaderboard rankings on both platforms.

• Pursuing MS in Cybersecurity Management and Policy at UMGC & Other Certifications

• United States Air Force Veteran

Time Stamps
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0:00 - Introduction
5:51 - Transferable Skills
12:15 - Rapid Fire Questions
16:24 - You Don't Need the OSCP
21:19 - Introverts & Social Engineering
25:37 - Pentest Rookie Mistakes
35:13 - Mental Health in Cybersecrity
39:45 - Final Hot Takes


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#Cybersecurity #infosec #informationsecurity #datasecurity #cybersecurityexpert #cybersecurityexperts #cybersecuritytips #cybersecuritytraining #hacking #hacking_pro #hacker #hackers #ethicalhacking #ethicalhacker #hackerman #hacked #penetrationtesters #penetrationtesting #pentesting #pentesting #pentesting #pentester #redteam #redteaming #offensivesecurity #security #technology #tech #IT #informationtechnology #Cyber #computerscience #LearnShareInspire #KyserClark #Kyser #OSCP #hackthebox #bugbounty #CTF #tryhackme #cybercareer #securitycertifications #techcareer

Music
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All music featured in this video is by Karl Casey @ White Bat Audio.

Disclaimer
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Attention viewers: This video 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.