In this episode, I speak with Jeff Man, a cybersecurity veteran with over 40 years of experience across NSA, red teaming, PCI, consulting, and industry leadership. Jeff shares a rare, ground-level view of what “security” actually means and why most organizations continue to get it wrong. We discuss his journey from solving puzzles to joining NSA, building the agency’s first red team, working on early cryptographic systems, and spending two decades teaching companies how to think about risk, data, and process. Jeff explains the critical difference between securing (technology, patching, fixing) and security (monitoring, process, diligence) and why the industry consistently overinvests in tools while underinvesting in thinking. This episode is a deep, practical, honest conversation about how security really works, and why mindset matters more than any product. Ideal for professionals across offensive, defensive, governance, and leadership roles who want to build long-lasting security programs. What You Will Learn (Key Takeaways): Why most companies fix technology but ignore processHow the cybersecurity mindset has shifted (and where it’s stuck)Stories from NSA, early crypto systems, and building the first red teamWhy PCI is misunderstood but extremely usefulThe difference between "securing" and "security"Why availability (not confidentiality) is today’s biggest problemThe importance of curiosity and the “hacker mindset”Why marketing shapes cybersecurity more than we admitHow to think, not just follow tools or trendsWhat keeps Jeff going after decades in the fieldTimestamps: 00:00 – Intro00:59 – Welcoming Jeff Man01:30 – Jeff’s journey from puzzles to NSA06:30 – Early cryptographic work & first software crypto system10:50 – Building NSA's first red team15:30 – Why companies don’t fix security even after pen tests17:30 – What organizations are getting wrong today20:10 – Why focusing only on technology never works22:30 – CIA triad misconceptions25:30 – Vulnerability overload & why “fix everything” is impossible28:30 – Securing vs. Security (monitoring, process, diligence)31:50 – Why process, not people, is the real failure point34:30 – Rethinking patching, compliance, and risk38:20 – How Jeff keeps himself informed today41:20 – Lessons from 900+ podcast episodes43:00 – The hacker mindset: curiosity, questioning, thinking49:20 – Why he continues speaking, podcasting, and mentoring51:21 – Closing thoughts