What happens when artificial intelligence moves faster than the organizations trying to control it?

In this episode of Joey Pinz Discipline Conversations, Joey Pinz sits down with Rob Gregory, Chief Information Security Officer at Optiv, to explore the hidden costs of AI, cybersecurity leadership, military experience, and the personal choices that shape success.

Rob shares how a last-minute decision to join the U.S. Army transformed his future, eventually leading him to cybersecurity work at the National Security Agency. He also reveals how military leadership taught him to make difficult decisions without having every answer.

🌟 Top 3 Highlights:

🤖 AI’s Hidden Costs: How an automated process generated a five-figure bill over one weekend, and why businesses are struggling with AI governance, security, and ROI.

🔐 The War on Passwords: Why Rob believes the cybersecurity industry spent years trying to fix passwords when it should have been eliminating them.

🎯 Leadership Through Uncertainty: How a consequential military cybersecurity decision shaped Rob’s approach to risk, responsibility, and leadership.

The conversation also explores quantum computing threats, family, personal growth, and the discipline required to balance professional ambition with a fulfilling life.