Will Foundation Models Kill Security Startups?
Did Anthropic just kill the AppSec industry? Following the announcement of Claude Code Security, a tool that finds, reasons about, and fixes code vulnerabilities, major security stocks dropped by 8% ....
5 Mar 59min
How to Build Your Own AI Chief of Staff with Claude Code
What if you could automate your entire work life with a personal AI Chief of Staff? In this episode, Caleb Sima reveals "Pepper," his custom-built AI agent to Ashish that manages emails, schedules mee...
11 Feb 47min
AI Security 2026 Predictions: The "Zombie Tool" Crisis & The Rise of AI Platforms
This is a forward-looking episode, as Ashish Rajan and Caleb Sima break down the 8 critical predictions shaping the future of AI security in 2026We explore the impending "Age of Zombies", a crisis whe...
28 Jan 1h
Why AI Agents Fail in Production: Governance, Trust & The "Undo" Button
Is your organization stuck in "read-only" mode with AI agents? You're not alone. In this episode, Dev Rishi (GM of AI at Rubrik, formerly CEO of Predibase) joins Ashish and Caleb to dissect why enterp...
23 Jan 51min
AI Security 2025 Wrap: 9 Predictions Hit & The AI Bubble Burst of 2026
It's the season finale of the AI Security Podcast! Ashish Rajan and Caleb Sima look back at their 2025 predictions and reveal that they went 9 for 9. We wrap up the year by dissecting exactly what the...
19 Des 20251h 3min
AI Paywall for Browsers & The End of the Open Web?
Cloudflare announced this year that AI bots must pay to crawl content. In this episode, Ashish Rajan and Caleb Sima dive deep into what this means for the future of the "open web" and why search engin...
10 Des 202539min
Build vs. Buy in AI Security: Why Internal Prototypes Fail & The Future of CodeMender
Should you build your own AI security tools or buy from a vendor? In this episode, Ashish Rajan and Caleb Sima dive deep into the "Build vs. Buy" debate, sparked by Google DeepMind's release of CodeMe...
3 Des 202550min
Inside the 29.5 Million DARPA AI Cyber Challenge: How Autonomous Agents Find & Patch Vulns
What does it take to build a fully autonomous AI system that can find, verify, and patch vulnerabilities in open-source software? Michael Brown, Principal Security Engineer at Trail of Bits, joins us ...
6 Nov 202558min
