The Hacker's Cache

#69 Why He Left a Safe Job to Hack Companies for a Living ft. Jim Schultz

The Hacker's Cache

Show Notes

In this episode of The Hacker’s Cache, Kyser Clark sits down with Jim Schultz, an OSCP-certified penetration tester, cybersecurity instructor, and consultant with over 15 years of experience. Jim shares his journey from taking apart his first family computer in the 90s to teaching hundreds of students and returning full-time to the world of ethical hacking and security consulting. They discuss how writing skills can make or break a pentester, what academia gets right (and wrong) about cyberse...

More from The Hacker's Cache

Sep 18, 2026

Is higher pay worth sacrificing stability, purpose, and peace of mind? In this cybersecurity Q&A episode, I share why leaving the Air Force for higher-paying private-sector cybersecurity work came with tradeoffs I did not fully appreciate at the time. I also answer whether government and public-sector cybersecurity jobs offer better job satisfaction, explain how to ethically tailor your LinkedIn job title to match the work you actually perform, discuss my updated cloud certification plan ...

Sep 4, 2026

More cybersecurity certifications will not automatically fix your career, raise your salary, or create the opportunities you want. In this episode of The Hacker’s Cache, Kyser Clark shares why he is slowing down after years of nonstop upskilling, pursuing certifications, and pushing toward bigger cybersecurity roles. He breaks down what actually moves the needle in cybersecurity careers: relevant hands-on experience, protecting yourself from burnout, understanding how employers evaluate resum...

Aug 25, 2026

Cybersecurity is evolving fast, but does that mean you need a degree, OSCP, or an endless stack of certifications to keep up? In this episode of The Hacker’s Cache, Kyser Clark sits down with returning guest Richie Vinson (4NU81X), an associate security researcher at Kobold.io and founder of Forsec, to talk honestly about breaking into cybersecurity through nontraditional paths. They discuss the current cybersecurity job market, AI security and AI red teaming, whether artificial intelligence ...

Aug 17, 2026

I barely went to any talks at DEF CON this year, and that was completely intentional. In this episode of The Hacker’s Cache, I break down my second DEF CON experience, why I believe networking and community can be more valuable than trying to attend every talk, how to make connections even if you’re introverted, what first-time attendees should expect, and whether DEF CON is actually worth the cost. I also share practical tips for surviving the conference, making the most of the villages and ...

Aug 5, 2026

The cybersecurity job market is more competitive than ever, even for experienced and highly certified professionals. In this episode of The Hacker’s Cache, I share the harsh reality of getting hired in cybersecurity, why breaking into penetration testing has become so difficult, and what employers expect from candidates entering offensive security roles. I also explain what companies charge for penetration tests, what new pentesters should expect on the job, which cybersecurity certifications...

See all episodes →