Today I speak with Yahoo CISO Sean Zadig – aka, the Chief Paranoid. Sean has had a long and varied career in cybersecurity, working both in law enforcement (at NASA!) and working security for Big Tech. I’ll ask Sean how we can teach our kids about cybersecurity, and how to protect them from the worst of the internet without compromising anyone’s privacy. I’ll also get his perspective on the relationship between Big Tech, user data, law enforcement and the Fourth Amendment.

Interview Notes

• The Paranoids (Yahoo): https://www.yahooinc.com/our-technology/paranoids 
• Suddenly a CISO: https://www.yahooinc.com/paranoids/suddenly-a-ciso-four-pieces-of-transitional-advice 
• Clipper Chip: https://en.wikipedia.org/wiki/Clipper_chip 

Further Info

• My book: https://fdsd.me/book 
• My newsletter: https://fdsd.me/newsletter 
• Support the mission: https://fdsd.me/support 
• Give the gift of privacy and security: https://fdsd.me/coupons 
• Get your Firewalls Don’t Stop Dragons Merch! https://fdsd.me/merch 

Table of Contents

• 0:00:13: Intro
• 0:01:20: Lingo
• 0:02:06: How did you become CISO at Yahoo?
• 0:05:38: Has AI made you job harder?
• 0:08:54: What the Paranoid ethos?
• 0:11:49: What a kids taught about cybersecurity?
• 0:14:05: How do we interest kids in cybersecurity?
• 0:17:35: How do we get kids to care about privacy?
• 0:21:42: Can we verify age privately?
• 0:25:06: Should parents control content restrictions?
• 0:28:36: Are kids echewing tech today?
• 0:31:51: How do we combat CSAM?
• 0:40:31: What’s it like working in law enforement?
• 0:47:14: Can we get Big Tech to collect less private data?
• 0:52:19: Is law enforcement skirting the 4th Amendment?
• 0:58:14: What’s next for The Paranoids?
• 1:00:01: Wrap-up
• 1:00:12: Patron podcast preview
• 1:01:10: Survey highlights
• 1:05:40: 2026 Milestones
• 1:06:49: Looking ahead