In this episode of The Hacker’s Cache, returning guest Ryan Daub shares his journey from IT support to offensive security and reveals practical advice on how to level up fast in your first cybersecurity role. We cover the importance of mastering fundamentals, documenting your work, learning from failures, and asking questions without fear. Ryan also opens up about leading internal pentests, preparing for the OSCP, transitioning toward red teaming, and why patience and persistence are key to long-term success in ethical hacking. Whether you’re starting your first pentesting job or planning your next certification, this episode delivers real-world insights you can apply immediately.
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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.
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