Securing the Workspace Attackers Already Live In with Rajan Kapoor

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1. 

   S6 · E420 · 31 Mar 2026 · 14 min

   What Happens When Attackers Collaborate More Than Defenders? Ron Eddings Reporting Live from RSAC Conference

   What happens when attackers collaborate better than defenders? Recorded live from RSAC 2026, this solo episode with Ron breaks down the biggest themes shaping cybersecurity right now, from organized threat groups and massive data breaches to the growing tension between productivity and control inside modern organizations. This conversation highlights a hard truth. The threat landscape is evolving through collaboration. From phishing-as-a-service platforms like Tycoon 2FA to supply chain breaches impacting entire ecosystems, attackers are sharing tools and moving faster than ever. But there’s…

2. 

   S6 · E419 · 20 Mar 2026 · 21 min

   RSAC 2026: Show Up or Fall Behind

   What does it mean when your smart doorbell becomes an entry point for surveillance? What happens when a single hacker can jailbreak every major AI model within hours of its release? And why are the same tools being used by both nation-state attackers and the defenders trying to stop them? In this solo episode, Ron Eddings breaks down the urgent case for practitioner unity in cybersecurity, from AI-powered jailbreaking and IoT surveillance creep to geopolitical cyber operations. With RSAC 2026 just around the corner, this episode is a rallying cry for the community to come together, share…

3. 

   S6 · E418 · 16 Mar 2026 · 37 min

   What’s Next After Building a $2.5B Cybersecurity Company with Dean Sysman

   What does it look like when a cybersecurity founder who built a $2.5 billion company decides to level up, again? Dean Sysman, co-founder of Axonius, sits down with Ron Eddings to pull back the curtain on what it really took to go from zero to $100M ARR in four and a half years, and what came next. Dean breaks down the founder mindset, the emotional weight of tying your identity to your company, and why he stepped into the Executive Chairman role while simultaneously pursuing a PhD in AI systems at Columbia University. He gets into how boxing taught him what solo performance reveals about…

4. 

   S6 · E417 · 6 Mar 2026 · 39 min

   Can AI Do Your Cyber Job? Post Your Job Req and Find Out with Marcus J. Carey

   Last episode, Ron and Marcus made predictions. This episode, they brought the receipts. A journalist built an app with vibe coding and got hacked on live television. A social network built entirely by AI (not a single line of human code!) exposed 1.5 million authentication tokens and private messages between agents. And 88% of organizations have already had an AI security incident, while barely 14% of deployed agents ever saw a security review. The warnings from last episode aged fast. Marcus J. Carey is back to talk about what that actually means for the people building right now, not the…

5. 

   S6 · E416 · 6 Mar 2026 · 40 min

   Why 69% of CISOs Are Ready to Walk Away with Anthony Johnson

   The CISO role isn’t the finish line, it’s a launchpad. 69% of security executives are eyeing the exit, and Anthony Johnson is proof that what comes next can be even bigger. Anthony Johnson, former Global CISO at JP Morgan and Fannie Mae, now founder and managing partner at Delve Risk, breaks down what really happens when a security leader stops buying tools and starts building companies. From the trap of unpaid advisory boards to why AI is eliminating the entry-level pipeline, Anthony delivers a no-nonsense look at career strategy, the future of fractional work, and why understanding how…

6. 

   E414 · 12 Feb 2026 · 42 min

   Beating “Checkbox Security” With Continuous Offense with Sonali Shah

   Security doesn’t fail because you missed a tool, it fails because “secure today” tricks you into relaxing tomorrow. This episode exposes why the real fight isn’t compliance… it’s whether your defenses hold up once attackers hit you with machine-speed pressure. Ron sits down with Sonali Shah, CEO of Cobalt, to talk about how human-led, AI-powered penetration testing is evolving into full-spectrum offensive security. Sonali shares how Cobalt can start a test in 24 hours, push findings directly into Slack/Teams and Jira, and use learnings from 5,000+ pentests a year to continuously sharpen what…

7. 

   S6 · E413 · 10 Feb 2026 · 38 min

   Turning Agent Chaos into a Command Center with Pedram Amini

   Text threads made AI feel personal, then agents made it productive, and suddenly “success” turns into chaos you can’t even track. In this episode, Ron sits down with Pedram Amini, creator of Maestro, to show what agent work looks like when you stop babysitting and start orchestrating. Pedram lays out why context windows are the limiter, why harnessing beats model-chasing right now, and how Auto Run executes task-docs with fresh context every iteration so agents can run for hours (or days) without melting down. Impactful Moments00:00 - Intro02:05 - Codex desktop sparks agent shift06:40 -…

8. 

   S6 · E412 · 29 Jan 2026 · 33 min

   Why MFA Isn’t the Safety Net You Think It Is with Yaamini Barathi Mohan

   Phishing didn’t get smarter, it got better at looking normal. What used to be obvious scams now blend directly into the platforms, workflows, and security controls people trust every day. In this episode, Ron sits down with Yaamini Barathi Mohan, 2024 DMA Rising Star, to break down how modern phishing attacks bypass MFA, abuse trusted services like Microsoft 365, and ultimately succeed inside the browser. Together, they examine why over-reliance on automation creates blind spots, how zero trust becomes practical at the browser layer, and why human judgment is still the deciding factor as…

9. 

   S6 · E411 · 25 Jan 2026 · 37 min

   When Cybercrime Learned How to Make Money and Never Looked Back with Graham Cluley

   Cybersecurity didn’t start as a billion-dollar crime machine. It started as pranks, ego, and curiosity. That origin story explains almost everything that’s breaking today. Ron sits down with Graham Cluley, one of the earliest antivirus developers turned trusted cyber voice, to trace how malware evolved from digital graffiti into organized financial warfare. From floppy disks and casino-style viruses to ransomware, extortion, and agentic AI, the conversation shows how early decisions still shape today’s most dangerous assumptions. Graham also explains why AI feels inevitable, but still deeply…

10. 

    S6 · E409 · 18 Jan 2026 · 37 min

    When Automation Outruns Control with Joshua Bregler

    AI doesn’t break security, it exposes where it was already fragile. When automation starts making decisions faster than humans can audit, AppSec becomes the only thing standing between scale and catastrophe. In this episode, Ron sits down with Joshua Bregler, Senior Security Manager at McKinsey’s QuantumBlack, to dissect how AI agents, pipelines, and dynamic permissions are reshaping application security. From prompt chaining attacks and MCP server sprawl to why static IAM is officially obsolete, this conversation gets brutally honest about what works, what doesn’t, and where security teams…