AI Security Podcast

When the CEO of Anthropic declares that human coding will disappear within six months, followed quickly by the death of software engineering itself, what does that mean for the future of cybersecurity? In this episode, Ashish and Caleb break down the massive paradigm shift caused by AI coding assistants like Claude Code. Caleb shares his firsthand experience building and deploying software where h...

Why do CISOs still struggle with asset intelligence in 2026? Despite decades of security tooling, most organizations still have a massive 40% "dark matter" blind spot in their environment and the explosion of ephemeral AI agents is only making it worse. In this episode, Ashish and Caleb sit down with Joe Diamond , CEO, Axonius to discuss the evolution of the asset space. We explore why t...

Why are security leaders terrified of connecting AI agents to production data? Because unlike humans, AI agents don't apply judgment, and they operate at machine speed, meaning they can relentlessly hunt down production credentials and do catastrophic damage before a human analyst even blinks. In this episode, Ashish and Caleb sit down with Graham Neray , CEO of Oso, to tackle the massive, uns...

Is your security team moving at the speed of your engineering team? In this special live recording of the AI Security Podcast from San Francisco, Ashish is joined by Nick Reva (Global Director, Engineering Security, DoorDash) and Shivani Doke to tackle the two most critical conversations in AI right now: Proactive Offensive Security and the evolution of GRC . In the first half, Nick explains why t...

Are autonomous AI agents operating unchecked in your enterprise? With the release of open source frameworks like OpenClaw, deploying an AI agent is now as simple as texting, but it comes with massive, unprecedented security risks . In this episode, Ashish and Caleb sit down with Sounil Yu , CTO and Co-Founder of Knostic (and creator of the Cyber Defense Matrix), to discuss the other side of agenti...

Is an AI agent's identity a workload or an action? Ashish spoke to Elie Bursztein , Distinguished Research Scientist and co-author of Google SAIF (Secure AI Framework) about how it is neither and that is exactly why our traditional security models no longer apply to the AI era . In this episode, Ashish sits down with Elie to explore the evolution of AI from a passive "brain in a jar"...

If your AI solution is just helping humans process the same amount of alerts a little faster, you haven't transformed anything, you've just created a faster hamster wheel. In this episode, Ashish and Caleb speak with Heather Ceylan , CISO at Box.com, about how she is leading a true, developer-first AI transformation within her security organization . Heather reveals the five strategic &quo...

In this episode, Ashish and Caleb discuss the internet-breaking preview of Project Mythos, an unreleased AI model from Anthropic that has shown an unprecedented, terrifying ability to reason through code and automatically generate working zero-day exploits .We dive into the conversations surrounding Project Glasswing, Anthropic's initiative to share this model with select partners (like Palo Alto...

With over 70 startups claiming to have built the perfect "AI SOC Analyst" or "AI Threat Hunter," how do you separate the real products from the vaporware? Recorded live at Decibel RSAC Founder Festival, Ashish and Caleb hosted a heated panel with Edward Wu (Founder & CEO, Dropzone AI ) and Lou Manousos (Co-Founder & CEO, Ent AI ). The group debates the controversial cla...

What does it actually look like to run security inside one of Europe's fastest-growing AI companies? In this episode, recorded live at the Munich Cybersecurity Conference (MCSC), Ashish Rajan sat down with  Igor Andriushchenko  Head of Security at  Lovable , the AI-native platform that lets anyone build and ship full applications without writing a line of code. Igor joined Lovable as employee...

RSA Conference 2026 is here and the AI agent hype machine is louder than ever. In this episode, Ashish and Caleb cut through the noise and arm CISOs, practitioners, and security teams with a clear-eyed view of what's actually happening in AI security this year. From the vendor floor at RSAC to the future of internal security automation, Caleb and Ashish speak about why 70% of "AI agent se...

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% .In this episode of the AI Security Podcast, Ashish and Caleb break down the reality behind the hype. Caleb explains why using AI for SAST (Static Application Security Testing) is "a no-brainer,&...

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 meetings, and even hires other AI experts to solve problems for him . Using Claude Code and a "vibe coding" approach, Caleb built a multi-agent system over a single holiday weekend, w...

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 2026 We explore the impending "Age of Zombies", a crisis where thousands of unmaintainable, "vibe-coded" internal tools begin to rot as employees churn . We also unpack controversial theory about the "circular economy" of token c...

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 enterprise AI adoption is stalling at the experimentation phase and how to safely move to production . Dev reveals the three biggest fears holding IT leaders back: shadow agents, lack of real...

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 industry got right (and wrong) about the trajectory of AI, providing a definitive "state of the union" for AI security. We analyze why SOC Automation became the undisputed king of real-...

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 engines as we know them might be dying . We explore Cloudflare's new model where websites can whitelist AI crawlers in exchange for payment, effectively putting a price tag on the world's...

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 CodeMender, an AI agent that autonomously finds, root-causes, and patches software vulnerabilities . While building an impressive AI prototype is easy, maintaining and scaling it into a produc...

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 to go behind the scenes of the 3-year DARPA AI Cyber Challenge (AICC), where his team's agent, "Buttercup," won second place. Michael, a self-proclaimed "AI skeptic," shares h...

Anthropic's August 2025 AI Threat Intelligence repor t is out, and it paints a fascinating picture of how attackers are really using large language models like Claude Code. In this episode, Ashish Rajan and Caleb Sima dive deep into the 10 case studies, revealing a landscape where AI isn't necessarily creating brand new attack vectors, but is dramatically lowering the bar and professionali...

What if the prompts used in your AI systems were treated as a new class of threat indicator? In this episode, Thomas Roccia , Senior Security Researcher at Microsoft, introduces the concept of the IOPC (Indicator of Prompt Compromise), sharing that "when there is a threat actors using a GenAI model for malicious activities, then the prompt... is considered as an IOPC". The conversation d...

Welcome to the 2025 State of AI Security. This year, the conversation has moved beyond simple prompt injection to a far more complex threat: attacking the entire ecosystem surrounding the LLM. In this deep-dive discussion, offensive security experts Jason Haddix ( Arcanum Information Security ) and Daniel Miessler ( Unsupervised Learning ) break down the real-world attack vectors they're seein...

Is the current AI hype cycle different from the ones that failed before? How do you build a security program for technology that can't give the same answer twice? This episode features a deep-dive conversation with Damian Hasse , CISO of Moveworks and a security veteran from Amazon's Alexa team, VMware, and Microsoft. Damian provides a practical blueprint for securing both traditional Mach...

Is generative AI a security team's greatest new weapon or its biggest new vulnerability? This episode dives headfirst into the debate with two leading experts on opposite sides of the AI dragon. We 1st published this episode on Cloud Security Podcast and because of the feedback we received from those diving into all things AI Security, we wanted to bring it to those who haven't probably ha...

What happens when your product, sales, and marketing teams can build and deploy their own applications in a matter of hours? This is the new reality of "Vibe Coding," and for CISOs, it represents both a massive opportunity for innovation and a significant governance challenge. In this episode, join Ashish Rajan and Caleb Sima as they move beyond the hype to provide a strategic playbook for securit...