Jon DiMaggio Takes You Undercover on the Dark Web Itself

Season 6 · Episode 32 · September 12, 2026

Expert Security Researcher, Jon DiMaggio, former National Security Agency (NSA) analyst, takes us under cover on the Dark Web, providing us insight in plain terms on: ransomware explained for small business and ransomware risks for small business, how cyber attacks stay undetected, how intelligence...

Expert Security Researcher, Jon DiMaggio, former National Security Agency (NSA) analyst, takes us under cover on the Dark Web, providing us insight in plain terms on: 

  • ransomware explained for small business and ransomware risks for small business, 
  • how cyber attacks stay undetected, 
  • how intelligence gathering is critical to security, 
  • secrets of cyber crime gangs, 
  • how stolen data is sold by cyber criminals, and
  • understanding the hacker mind.

Don’t miss Jon’s book, The Art of Cyber Warfare: https://a.co/d/a2r7C5G

 

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The Moving Target Trilogy. Book 3 to be released September 22nd, 2026. Start with any of them. Be a Moving Target.

Special Author pricing (30% off)

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Hosted by David Dean Mauro. Former trial lawyer, AI Security Advisor, FBI InfraGard member, VP of Strategic Growth at NetGain Technologies, and author of the Moving Target Trilogy (#1 Amazon Hot New Release, 2026).

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Chapters

  • 0:00 Jon DiMaggio Takes You Undercover on the Dark Web Itself
  • 4:13 The Evolution of Ransomware as a Service
  • 4:25 Introduction to Cybercrime and Ransomware
  • 7:32 Ransomware Explained For Small Business
  • 10:27 The Role of Affiliates and Initial Access Brokers
  • 13:22 Challenges in Cybersecurity and Detection
  • 17:17 The Impunity of Ransomware Gangs
  • 20:33 Motivations Behind Ransomware Attacks
  • 23:28 The Impact on Healthcare and Critical Services
  • 27:24 How Stolen Data Is Sold By Cyber Criminals
  • 34:14 Under Cover on Dark Web
  • 37:09 The Dark Web's Impact on Business
  • 40:04 The Consequences of Data Breaches
  • 42:29 The Complexity of Cybersecurity Breaches
  • 45:55 The Reality of Paying Ransom
  • 48:13 The Toll of Cyber Warfare on Professionals
  • 50:26 Current Landscape of Ransomware Groups