Why Companies Still Pay Ransoms (And How AI Makes It Worse) w/ Joshua Nicholson, CEO of DarkStack7

Joe Erle sits down with Joshua Nicholson, Founder & CEO of DarkStack7 and Host of Cybersecurity America Podcast, to break down the critical incident response mistakes that leave companies with no choice but to pay ransoms. Joshua exposes the most common breach vulnerabilities still being exploited in 2026 including unpatched firewalls, missing MFA, excessive local admin rights, and AI tools like Microsoft Copilot leaking confidential HR data. He explains why identity has become the new security perimeter, how removing local admin rights stops lateral movement, and why every organization needs pre-provisioned break-glass access before a crisis hits. You'll also learn: How to fix dangerous logging and licensing blind spots Practical ways to patch systems without causing panic Lessons from real disaster recovery failures How DDoS attacks are used to increase ransom pressure A simple tabletop exercise playbook that actually works How strong cyber hygiene helps satisfy cyber insurance underwriters What Happens when AI Hacks Collide Timestamps: 00:35 – Intro Teaser 02:38 – MFA and Security Hygiene 06:04 – Identity Perimeter Shift  06:55 – Local Admin and LAPS 08:25 – Least Privilege Culture 12:00 – Patching Without Panic 15:59 – Disaster Recovery Lessons 18:59 – DDoS and Ransom Pressure 22:00 – Tabletop Exercise Playbook 25:27 – Logging and Licensing Gaps 27:37 – Finding Joshua and Services 28:42 – AI Breaches and Microsoft Copilot 30:46 – AI Risks and Market Crash 33:40 – Wrap Up and Thanks Guest: Joshua Nicholson | Founder & CEO, DarkStack7 LinkedIn: https://www.linkedin.com/in/joshuarnicholson Cybersecurity America Podcast https://www.youtube.com/@cybersecurityamerica\_show Hosts: Joe Erle | Cyber Group Practice Leader, C3 Risk & Insurance Services LinkedIn: https://www.linkedin.com/in/joeerle X: https://x.com/joe\_erle TikTok / Instagram / Facebook: @itscyberjoe   Ransomware Rewind is a practical cybersecurity podcast focused on real-world cyber risk, incident response, and resilience. We talk to the people on the front lines so you can protect your business before the next attack. Like, subscribe, and hit the bell for more insights on ransomware, cyber insurance, and building a stronger security posture. You can also listen on Spotify or Apple podcasts!  I appreciate your support! Thx!   #Ransomware #CyberSecurity #IncidentResponse #MFA #IdentitySecurity #LeastPrivilege #CyberInsurance #AISecurity #MicrosoftCopilot #DarkStack7 #RansomwareRewind