In this episode of Terminal Value, I'm joined by Cy Khormaee, founder and CEO of Aegis AI, an AI-native email security company that recently raised a $36 million Series A led by Battery Ventures, to discuss why email security is becoming an AI-versus-AI problem, how personalized threats are bypassing legacy rules, and what changes when AI begins handling the intelligence layer of cybersecurity.

We cover how email security evolved from reputation-based appliances to machine learning and rules, why LLM-based reasoning can investigate each message in context, how Aegis uses specialized multi-agent models instead of frontier APIs, why proprietary email data creates a compounding advantage, how automated incident response can shrink exposure from hours to milliseconds, what security buyers need to trust autonomous systems, why AI-native architecture can challenge incumbents, how the category could expand from protecting the corporate inbox to protecting the person, and why Cy hires for slope in an uncertain future.

0:00 Hook: Why email security is becoming AI versus AI
0:40 Intro to Cy Khormaee and Aegis AI
1:45 How email security evolved from reputation and rules to AI
4:55 How AI is making phishing attacks more personalized and harder to detect
9:35 How Aegis uses multi-agent reasoning to stop email threats
12:50 Why rule-based security breaks as threats change faster
15:45 How proprietary email data creates a compounding AI advantage
18:00 How automated response changes accountability and earns trust
25:10 Why Aegis builds specialized models instead of relying on frontier models
31:45 How AI-native architecture can overcome incumbent data advantages
39:25 From securing email to protecting the person
41:15 Why Cy hires for slope in an uncertain AI future
42:50 Closing takeaways