In this episode, Jackie Shoback—Co-Founder of 1414 Ventures and seasoned C-suite leader—joins Greg to explore how cybersecurity has evolved from a back-office IT function into a core business strategy. Drawing on decades of experience across enterprise and financial services, Jackie breaks down why digital identity and trust are now at the center of modern security, and how organizations must rethink data as both an asset and a risk.

The conversation dives into the growing importance of identity-driven security, the shortcomings of current privacy practices, and the role of boards and executives in building a true culture of security—not just checking compliance boxes. With insights on emerging threats, AI, and the future of digital trust, this episode offers a strategic lens for leaders navigating today’s rapidly evolving cyber landscape.