AI Hacking Risks, $100K CMMC Grants, and the Fractional CISO Debate cover art

AI Hacking Risks, $100K CMMC Grants, and the Fractional CISO Debate

AI Hacking Risks, $100K CMMC Grants, and the Fractional CISO Debate

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In this episode of The Other Side of the Firewall, hosts Ryan, Shannon, and Chris dissect a trending security report detailing how a low-skilled attacker easily hijacked a Claude AI instance to breach 14 companies by simply tricking the AI's guardrails. The team then shifts gears to discuss a new Senate NDAA proposal offering up to $100,000 in CMMC grants to help small defense contractors manage the steep costs of compliance, followed by a fiery debate on whether the rise of part-time, "fractional" CISOs is a smart budget move or a dangerous trend fueled by executive burnout and SEC liability fears. Finally, the crew decompresses by sharing their recent personal highlights, diving into everything from Italian cheese wheels and intense kettlebell training to the latest anime and running Cyberpunk 2077 via cloud gaming. Article: Low-skilled attacker used Claude, Codex to breach 14 companies https://www.helpnetsecurity.com/2026/06/17/ai-agents-offensive-cyber-operations-claude-codex/?fbclid=IwZXh0bgNhZW0CMTAAYnJpZBExRmN0RFJDWEUzaUlaQ1dQanNydGMGYXBwX2lkEDIyMjAzOTE3ODgyMDA4OTIAAR4E3yG7BOaMeTYFubhdWQ_VIe4dFT44y-rT81FKg7V-SI5kcjcb1RWQ6xGULA_aem_8VhuxrLpU8NGw90c2z2F4g Senate NDAA proposes CMMC grant program https://federalnewsnetwork.com/technology-main/2026/06/senate-ndaa-proposes-cmmc-grant-program/?fbclid=IwZXh0bgNhZW0CMTAAYnJpZBExRmN0RFJDWEUzaUlaQ1dQanNydGMGYXBwX2lkEDIyMjAzOTE3ODgyMDA4OTIAAR4Aj2tVqytcIddIhgYsDnOqhU3C2bFQJfvK6bCubRb6Irl1e-RsrCyXf47h8g_aem_flEvM7hdgC50H6QHxfc4WQ CISOs Not Likely to Disappear https://www.darkreading.com/cybersecurity-operations/stressors-ai-changes-cybersecurity-teams?fbclid=IwZXh0bgNhZW0CMTAAYnJpZBExRmN0RFJDWEUzaUlaQ1dQanNydGMGYXBwX2lkEDIyMjAzOTE3ODgyMDA4OTIAAR5iE2M_iy9f90Ot-N5J6yTCoGvB03tT6inGBuBHKpGzTq0-Q_6Vcls5sUZkJw_aem_YQTYrJHf8yoZ6ZBmBjcUQg Buy my book: https://www.theothersideofthefirewall.com/ Please LISTEN 🎧 LIKE 👍🏿 and SHARE ❤️ Thanks! Socials: Website - www.ramcyber.io Heroes Media Group: https://www.heroesmediagroup.com/shows/the-other-side-of-the-firewall/ Audio - https://podcasts.apple.com/us/podcast/the-other-side-of-the-firewall/id1542479181 YouTube - https://www.youtube.com/@theothersideofthefirewall7511 ReppedFLIX - https://lnkd.in/eVis2CbS WDJY 99.1 FM: https://www.wdjyfm.com/ TuneIn: https://lnkd.in/e2crcZU8 Facebook - https://www.facebook.com/profile.php?id=61556539026086 Instagram - https://www.instagram.com/theothersideofthefw X (Twitter) - https://twitter.com/Ask_a_CISSP TikTok - https://www.tiktok.com/@ryanwilliams683 Medium - https://medium.com/@ryanwilliamssenior Subscribe to LinkedIn Newsletter - https://www.linkedin.com/build-relation/newsletter-follow?entityUrn=7172626552545865728 LinkedIn - https://www.linkedin.com/company/the-other-side-of-the-firewall/ Ryan on Twitter, LinkedIn, Clubhouse, and Threads - @ryrysecurityguy | https://www.ryanwilliamssenior.com/ Chris on LinkedIn - https://www.linkedin.com/in/chrisabacon/ Chapters 00:00 Introduction to Cybersecurity Trends 00:49 AI's Role in Cyber Attacks 10:37 Government Support for Cybersecurity Compliance 22:15 The Evolving Role of CISOs in Cybersecurity 36:27 The Challenges of Transitioning Military to Civilian Roles 37:56 The Value of Fractional CISOs 39:13 Navigating Hiring Challenges in Cybersecurity 40:31 The Importance of Experience in Leadership Roles 42:15 Understanding the CISO's Broader Responsibilities 43:15 The Rise of Fractional Executives 45:19 Personal Updates and Family Time 48:15 Dining Experiences and Family Activities 48:33 Media Consumption and Entertainment Preferences 52:09 Gaming and Cloud Technology Insights #cybersecurity #claudeai #vciso
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