In this episode of the Be Fearless Podcast, Larry Whiteside Jr, Co-Founder and President of Confide, sits down with SquareX Field CISO John Carse to discuss the real risks facing today’s CISOs. Drawing from three decades of experience across the U.S. military, the Pentagon, and Fortune 500 leadership roles, Larry explains why the CISO role is the most exposed and misunderstood position in the C-suite. They dive into cybersecurity governance, power dynamics with executives, vendor hype, regulatory pressure, AI disruption, and why security leaders are often blamed despite lacking authority.

00:00 How a Pentagon analyst role turned out to be for Chief of Information Warfare
19:28 "You are not greater than the good of the entire building"
27:48 Why the cybersecurity buying process is fundamentally broken
35:28 Can, or should a CISO be likable?
43:32 Larry's leap to entrepreneurship
50:06 Changes in IT landscape: Cloud, SaaS, AI
1:00:23 Narcissistic tendencies in cyber leadership
1:11:39 Career advice and how to avoid burnout

🔔 Follow Larry and John on:
https://www.linkedin.com/in/larrywhitesidejr/
https://www.linkedin.com/in/johncarse/

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