Thomas Richard chats with Michael Greenlaw, Founder & CEO, FedRock

Michael Greenlaw on AI, DevSecOps, and FedRAMP Automation: Speed, Risks, and the Need for Fundamentals

Tom and Michael discuss Microsoft’s strategy and licensing shifts pulling organizations toward Windows and Azure, and the frustration of incompatible cloud service naming across AWS/Azure/GCP. Michael describes using Claude to learn and build with LLMs rapidly, calling it “fast Google,” but warns about hallucinations, compounded errors in chained tasks, human limits in reviewing massive AI-generated code, poor handling of branching strategies, and the need for humans to own architecture and fundamentals.

They debate layoffs attributed to AI versus post-COVID overhiring and shareholder optics, and note AI’s growing impact on vulnerability discovery and exploitation.

Book recommendations: “How to Win Friends and Influence People” (Dale Carnegie), “The Trusted Advisor,” and “Thinking in Bets.”

00:00 Welcome and Intro

00:39 Career Path Update

01:25 Why Windows Again

05:41 Cloud Naming Frustrations

07:27 Keeping Up With Titles

09:12 AI Learning Acceleration

11:36 Curiosity in Hiring

15:39 Market Whiplash Era