The Capital One Breach and the 1% Security Gap Nobody Fixed

The Capital One Breach and the 1% Security Gap Nobody Fixed

Ross Young was inside Capital One when the 2019 breach happened and he's breaking down what the headlines got wrong. From WAF misconfigurations to AI-powered attacks moving at machine speed, this episode is a tactical masterclass for security leaders who want to stop wasting budget and start building real defences. Ross Young is a former intelligence officer turned enterprise CISO. He was at Capital One during the 2019 breach, authored Cybersecurity's Dirty Secret: Why Most Budgets Go to Waste, and is now co-founder & CEO of Clear Capabilities, building AI agents to automate the parts of security that drain teams dry. In this episode, Ross explains: ◼ The exact WAF misconfiguration that enabled the Capital One breach and why it's probably still hiding in your environment ◼ Why your security tools are likely only 40–72% effective, and how to calculate your true effective protection score ◼ Which security categories are largely security theater (DLP, third-party risk management) and where budget should actually go ◼ How AI is shifting the speed of attacks vs. defenses and what defenders must do right now to keep up ◼ Why AI agents need kill switches, audit trails, and rollback processes before they ever go live Time Stamps (00:00) Introduction: Ross Young's Path From Offense to CISO (00:29) Inside the 2019 Capital One AWS Breach (07:14) Evidence Every CISO Should Collect After a Breach (08:26) The Swiss Cheese Firewall Problem (11:17) Misaligned Incentives Between Developers and Security (13:10) Risk Acceptance: The MRI Machine and the CFO's Math (17:55) Murder Boards: Killing Underperforming Security Tools (24:18) Why Vendor Choice Matters Less Than Configuration (28:32) Where Security Budgets Should Actually Go (32:39) AI Is Closing the Attacker-Defender Speed Gap (36:25) Stopping Deepfakes and Phishing With Process, Not Tools (43:51) AI Agents Are the New Phishing Target (47:37) Building a Kill Switch for Rogue AI Agents (51:51) Introducing the OWASP Threat and Safeguard Matrix (58:50) One Thing Every CISO Should Fix This Week (59:48) Ross's New Venture: Clear Capabilities Connect with Ross Young on LinkedIn: https://www.linkedin.com/in/mrrossyoung/ [https://www.linkedin.com/in/mrrossyoung/] Hosts ⬇️ Yegor Sak: https://www.linkedin.com/in/yegor-sak-725330b2/ [https://www.linkedin.com/in/yegor-sak-725330b2/] Alex Paguis: https://www.linkedin.com/in/alex-paguis-53a21815/ [https://www.linkedin.com/in/alex-paguis-53a21815/] Powered by Control D [https://controld.com/]

Navy Officer Reveals the Threat Modeling Mindset Most Cybersecurity Teams Are Missing

Ben Lipczynski is the Director of Security and Regulatory Services at Origina and a former British Royal Navy officer with 12 years operating nuclear submarines and global networks. He brings an operator-level perspective on what separates a contained incident from a months-long operational nightmare. In this episode, Ben breaks down why patching is not a silver bullet, why legacy systems are more defensible than most teams assume, and what the submarine service taught him about knowing your critical systems before an attacker finds them for you. He explains: ◼ Why siloed teams and poor system knowledge cause more breaches than sophisticated attacks ever do ◼ Why upgrading to the latest version often introduces more vulnerabilities than it removes ◼ How 700 scan findings came down to 20 real actions after proper contextual analysis ◼ Why the CVE volume problem is about to get significantly worse and what to do about it ◼ Why defense in depth, not patching, is the only strategy that holds up when an attacker gets inside Time Stamps: (0:00) Introduction (0:53) What corporate security teams get wrong vs. the military (2:22) The submarine mindset: 90% training, 10% operations (4:48) Operational clarity in the military: everyone knows the mission and their role (6:59) Military structure vs. corporate agility — opposites or the same need? (10:38) Why Ben left the Navy for cybersecurity (14:32) "Take a marching pace" — thinking before acting in incident response (18:09) The iPad water treatment plant story — OT connectivity creep in the real world (25:30) The myth of N-minus-one: legacy doesn't mean insecure (28:10) Open source dependency risk — 60% of vulnerabilities aren't in the core code (31:01) Slop squatting: attackers pre-registering AI-hallucinated package names (33:00) What to do when you can't patch — contextual risk-based defense in depth (36:26) The patch validation problem — exploits now arrive within hours of a CVE (44:00) Fully patched, still taken down — architecture beats updates (51:26) Log4J case study: why deleting the library beat the patch cycle (55:23) Practical advice for security teams managing legacy systems (1:02:22) The CVE volume crisis — is the current patching model even tenable? (1:07:21) Bold prediction: CVE text itself will become an attack vector for AI agents Connect with the speakers ⬇️: Ben Lipchinski: https://www.linkedin.com/in/benlipczynskisecurity/ [https://www.linkedin.com/in/benlipczynskisecurity/] Yegor Sak: https://www.linkedin.com/in/yegor-sak-725330b2/ [https://www.linkedin.com/in/yegor-sak-725330b2/] Alex Paguis: https://www.linkedin.com/in/alex-paguis-53a21815/ [https://www.linkedin.com/in/alex-paguis-53a21815/] Powered by Control D [https://controld.com/]

ISO 27001 Expert: Why Compliance Doesn't Equal Security For CISOs

John Verry is the Managing Director at CBIZ Cybersecurity, ISO 27001 certified lead auditor since 2006, and has guided hundreds of organizations through ISO 27001, SOC 2, CMMC, FedRAMP, and HITRUST. He has seen firsthand what separates organizations that get genuinely secure from those that just collect certifications. In this episode, John breaks down the gap between compliance and actual security, why shadow AI is already embedded in tools your team uses daily, and why agentic AI is the risk no CISO is truly prepared for yet. He explains: ◼ Why you can be fully compliant and completely insecure at the same time ◼ Why operationalizing your security program inside tools your team already uses matters more than buying another GRC platform ◼ How 65% of SaaS platforms now have AI built in and why most organizations have no inventory of it ◼ Why the EU AI Act's August 2026 deadline is real and what organizations need to do now ◼ Why agentic AI shifts the risk from hallucination to autonomous business decisions made at scale without a human in the loop Timestamps (00:00) Introduction (06:27) Meet John Verry: Managing Director at CBiz Cybersecurity (07:47) What compliance theater actually means and why it matters (09:34) Security is a journey, compliance is a destination (12:30) The most common mistakes companies make after getting certified (15:07) What it actually takes to operationalize a security program (17:34) The merchants of complexity problem and why less tooling wins (20:50) Third party risk management and the hidden operational debt of every new vendor (22:19) What shadow AI is and why most organizations still do not know they are using it (28:21) How to balance moving fast on AI with slow-moving compliance frameworks (31:40) Why ISO 27001 updates slowly and why that might actually be a good thing (36:41) How to risk model different types of AI from Grammarly to agentic systems (40:14) Why shadow AI is lower risk than deeply integrated AI but still dangerous (43:29) Sycophantic AI behavior, what causes it, and why it creates real danger (52:29) AI coding AI, the hard takeoff, and the model collapse problem (54:24) EU AI Act deadlines, ISO 42001, and why AI compliance urgency is now (58:44) How ISO 42001 works as an extension of ISO 27001 (01:01:27) When auditors do not understand AI governance and certifications become theater (01:02:28) The main blocker stopping CISOs from escaping compliance theater (01:05:41) The next 12 to 18 months: why the era of agentic AI is already here (01:07:48) Closing thoughts: What should actually scare every CISO right now Connect with John Verry on LinkedIn https://www.linkedin.com/in/jverry/ [https://www.linkedin.com/in/jverry/] Hosts ⬇️ Alex: https://www.linkedin.com/in/alex-paguis-53a21815/ [https://www.linkedin.com/in/alex-paguis-53a21815/] Yegor: https://www.linkedin.com/in/yegor-sak-725330b2/ [https://www.linkedin.com/in/yegor-sak-725330b2/] Powered by Control D [https://controld.com/]

EX-FBI Agent Breaks Down Breach Realities: Identity Is The New Malware

Devon Ackerman is the Global Head of Digital Forensics and Incident Response at Cyber Reason and a former FBI Supervisory Special Agent focused on counterintelligence and cyber investigations. He is also the author of Diving In: An Incident Responder's Journey and one of the most experienced breach investigators working today. In this episode, Devon walks Alex and Yegor through exactly how modern intrusions unfold in the real world, from the first point of entry to full compromise, and what most organizations are still completely missing until the damage is done. He explains: ◼ Why attackers ditched malware and are stealing identities to hide inside normal user behavior ◼ How one phone call to a help desk bypassed MFA and gave full network access without a single alert ◼ Why phishing kits intercept your authentication token, not your password ◼ Why hardware keys stop most kill chains cold and where that still breaks down ◼ The four threat actor categories and why each one requires a different defensive response Time Stamps (00:00) Devon Ackerman Introduction (01:48) Why digital forensics and incident response belong together (04:28) How modern investigations have changed in the last 5 years (06:49) Are attackers moving faster than defenders? (08:41) Can digital forensics become proactive? (11:31) Will AI turn cyber defense into a war of bots? (14:50) Why security adoption still lags behind new threats (16:43) Identity becomes the primary attack surface (19:56) War story: help desk social engineering, password resets, and disabled MFA (22:52) A real vulnerability exploited within 12 hours (25:18) What happens when CVE-to-exploit timelines shrink to minutes (28:29) How adversary-in-the-middle MFA phishing works (33:16) Why MFA bypass is really about intercepting authentication (35:54) Hardware keys and where phishing kill chains usually stop (39:14) Hacktivists, nation-states, organized crime, and initial access brokers (42:47) The economics of selling access vs exploiting it yourself (46:56) Devon’s final advice for defenders: reduce blast radius Connect with the speakers ⬇️ Devon: https://www.linkedin.com/in/devonackerman/ [https://www.linkedin.com/in/devonackerman/] Yegor: https://www.linkedin.com/in/yegor-sak-725330b2/ [https://www.linkedin.com/in/yegor-sak-725330b2/] Alex: https://www.linkedin.com/in/alex-paguis-53a21815/ [https://www.linkedin.com/in/alex-paguis-53a21815/] Powered by Control D [https://controld.com/]

Cyberwarfare Is Not What CISOs Think: How to Protect Your Crown Jewels

Matan Eli Matalon breaks down AI-driven cyberwarfare, Iran-linked threat intelligence, and what CISOs must protect when attackers are trying to cause disruption. This episode had to pause mid-recording after Matan, a former CISO who reverse-engineered Iran’s Handala malware, received a missile warning and had to take shelter. We picked the conversation back up the next day. Matan Eli Matalon breaks down what cyberwarfare actually looks like on the ground right now: why Iran-linked groups are winning with basic techniques and propaganda, how AI is giving attackers a speed advantage defenders can't match, and what CISOs need to stop doing if they want to protect what actually matters. He explains: * Why groups like Handala choose quantity over sophistication and how that makes them harder to defend against * How AI removes friction for attackers without changing the attacks themselves and why defenders can't keep up * Why protecting everything equally is the fastest way to protect nothing * The 3-step CISO framework: define failure, map every attack path to it, validate it's closed Timestamps: • (00:00) Intro - Cyberwar is already here • (03:00) Disruption over dollars • (06:45) The Handala playbook exposed • (08:07) Inside Handala’s malware • (10:29) AI didn’t make hackers smarter, it made them faster • (12:20) Anthropic’s leaked “Mythos” model • (13:48) Stop protecting everything, protect what can kill you • (18:00) AI is breaking your security perimeter from within • (22:20) The house analogy that changes how CISOs think • (34:25) The CISO isn’t the department of no • (46:45) Agentic AI is a black box and CISOs hate it • (51:05) Slop squatting: the attack no one’s talking about • (54:00) The Iranian hack that almost took everything down • (1:00:00) When the goal is deletion, not data theft • (1:03:18) The backup that wasn’t • (1:06:30) The 3-step framework every CISO needs • (1:08:25) Why this 28-year-old chose defense over offense • (1:10:50) Cybersecurity in 3 years: Matan’s prediction Connect with Matan Eli Matalon on LinkedIn [https://www.linkedin.com/in/matan-eli-matalon-413081186/] Powered by Control D [https://controld.com/]