From NSA to CISO: A Conversation with Ira Winkler

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About The Guest:
Ira Winkler is a renowned cybersecurity expert with over 30 years of industry experience. He started his career at the National Security Agency (NSA) and has since held various roles in the field of cybersecurity, including chief security strategist at HP and chief security architect at Walmart. He is currently the CISO at CYE, a cybersecurity company. Winkler is also the author of several books, including "You Can Stop Stupid" and "Security Awareness for Dummies."

Ira Winkler, a cybersecurity expert with over 30 years of industry experience, joins the podcast to discuss the cybersecurity skills shortage and the importance of practical experience in the field. He emphasizes the need for cross-training individuals with computer backgrounds in cybersecurity rather than relying solely on certifications or degrees. Winkler also highlights the value of soft skills and critical thinking in the cybersecurity field. He shares his perspective on the misconception that anyone can enter the field without experience or credentials and explains the importance of understanding programming and mathematical principles in certain cybersecurity roles.

Key Takeaways:

  • Practical experience and cross-training individuals with computer backgrounds are more valuable than certifications or degrees in cybersecurity.
  • Soft skills and critical thinking are essential in the cybersecurity field.
  • Understanding programming and mathematical principles can enhance cybersecurity skills.
  • Machine learning may automate certain cybersecurity tasks, but a deeper understanding of the underlying principles is still necessary.


  • "Our job is to stop stupid. Our job is to patch stupid." - Ira Winkler
  • "You're competing against people who know how to program, who have college degrees, who set up their home labs." - Ira Winkler
  • "A job might have no requirements, but you're likely going to be competing against people who do have qualifications." - Ira Winkler

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From NSA to CISO: A Conversation with Ira Winkler
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