CyberWire Daily Jon DiMaggio: Two roads diverged. [Strategy] [Career Notes]
Dec 7, 2025
Jon DiMaggio, Chief Security Strategist at Analyst1, shares his journey from aspiring actor to cybersecurity expert. He highlights his self-taught approach to technology and how early career hurdles, including a crucial firing, pushed him to deepen his skills. Jon emphasizes the importance of resilience, networking, and self-driven learning in building a successful career. His experience in signals intelligence shapes his unique perspective on blending technical expertise with analytical insights, inspiring others to break into the cybersecurity field.
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Self-Taught Networking Batcave
- Jon DiMaggio taught himself to build and configure networks using surplus Cisco gear in his apartment.
- He used hands-on practice and certifications (CCNA, Microsoft) to prepare for his first roles.
Career Pivot Into Intelligence
- A program manager recruited Jon into a new role combining technical skills and intelligence reporting.
- That shift taught him how to
Fired, Then Accelerated
- Jon left government work and struggled first in the private sector where the role didn't fit his style.
- Being let go led him to Symantec, which reignited and accelerated his career.