On this week’s Ask a CISSP special episode of The Other Side of the Firewall, I talk with Air Force veteran and cybersecurity leader Ahmad Rashaan Austin about his journey from zero computer skills to founder of Cy3 Security, LLC. We explore risk management, responsible AI adoption, leadership communication, and his new book, The Boundaryless Enterprise. If you’re building a cyber career or leading tech teams, this episode delivers actionable insights straight from the front lines. Check it out on your favorite podcast platform!

Buy Ahmad R. Austin's The Boundaryless Enterprise: Redesigning Oversight for the Age of Intelligent Systems
https://a.co/d/dfCToig

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Chapters
0:00 – Intro to the Episode & Guest
1:00 – Ahmad’s Background: Decatur Roots & Military Journey
3:00 – Military Life & Transition into IT
5:00 – From No Computer Skills to Cyber Career
7:00 – Starting in Cybersecurity as a Contractor
9:00 – Founding Cy3 Security, LLC
10:30 – Services Offered by Cy3 Security
12:00 – Risk Management vs. AI Hype
14:00 – The Story Behind The Boundaryless Enterprise
16:00 – Why Organizations Fail at Governance
18:00 – AI Agents, Identity, and Risk
20:00 – The Dangers of AI Drift & Inaccurate Output
23:00 – Using Architecture to Govern AI
26:00 – The Hallucination Problem with AI Tools
29:00 – Third-Party Risk & Vendor Transparency
31:00 – Military Risk Culture vs. Private Sector
34:00 – Why Companies Need Better Risk Imagination
36:00 – Transitioning Into Cyber Entrepreneurship
38:00 – How Ahmad Recharges: Training in Wing Chun Kung Fu
40:00 – Book Release Details & Where to Find Ahmad
41:00 – Final Thoughts and Episode Wrap-Up

#cybersecurity #aigovernance #BoundarylessEnterprise