Why Doing the Basics in Cyber Is So Hard—and So Necessary | Ross Haleliuk

In this episode of The Segment, Raghu sits down with Ross Haleliuk—Co-Founder & CEO of a stealth startup, author of Cyber for Builders, and host of Inside the Network and Venture in Security to unpack why most security failures aren’t caused by a lack of tools, but by a failure to execute the fundamentals.

Ross brings a pragmatic, business-first lens to cybersecurity, cutting through hype, buzzwords, and so-called “silver bullets” to focus on what actually works in the real world. Together, they explore why breaches still happen even in organizations that invest heavily in security and why that investment still matters.

In this conversation, you’ll learn:

• Why most cyber breaches still come down to security fundamentals, not next-gen tools
• Why cybersecurity has become a “market for silver bullets”—and what that means for buyers and vendors
• How misaligned incentives across engineering, IT, sales, and security undermine long-term security
• Why compliance should be treated as a baseline, not the finish line
• How to think about security ROI in a way executives actually understand
• How to evaluate AI in cybersecurity without getting lost in the hype
  Why security leaders must learn to lead without authority, similar to product managers
• What gives Ross optimism about the future of cybersecurity heading into 2026