From Military to Cybersecurity: John Rodriguez on Mentorship, Ransomware, and Building Resilient Defenses

From Military to Cybersecurity: John Rodriguez on Mentorship, Ransomware, and Building Resilient Defenses

06/17/2025 | Phillip Wylie |

The Phillip Wylie Show episode featuring John Rodriguez from Cyber Dagger:

πŸ” Episode Summary:
In this episode of The Phillip Wylie Show, cybersecurity expert John Rodriguez, founder of Cyber Dagger, shares his inspiring journey from the military to launching a cybersecurity company. John dives into the critical challenges faced by educational institutions and nonprofits, the growing threat of ransomware, and why a holistic security strategy is vital. He emphasizes the power of mentorship, community service, and continuous hands-on learning in shaping the next generation of cybersecurity professionals. This conversation is packed with real-world insights, career tips, and practical approaches to improving cyber defenses.

βœ… Key Takeaways:

  • Giving back through cybersecurity strengthens communities and builds talent pipelines.

  • Diverse backgrounds, like military service, offer valuable skills for cyber careers.

  • Schools and nonprofits are prime targets for ransomware and must prioritize security.

  • Mentorship and guidance are essential to developing future cyber leaders.

  • Adversarial thinking is crucial for effective red teaming and threat response.

  • Building in-house tools and platforms can greatly improve cyber resilience.

  • Don’t rushβ€”take time to master the fundamentals and stay curious.

🎧 Memorable Sound Bites:

  • “It’s important that we stay together.”

  • “Don’t rush through it.”

  • “Leave it better than what you found it.”

πŸ•’ Episode Chapters:
00:00 – Intro to John Rodriguez & Cyber Dagger
02:22 – From Military to Cybersecurity
04:45 – Mentorship’s Role in Cybersecurity
07:05 – Securing K–12 and Nonprofits
09:31 – Ransomware Realities in Education
12:16 – Why Incident Response Matters
15:48 – Pen Testing vs. Incident Response
18:18 – Real-World Testing in Cybersecurity
21:38 – Role of EDR & Security Platforms
24:53 – Military Influence on Cyber Strategy
27:49 – Holistic Security: Why It Matters
31:05 – Building In-House Security Tools
36:09 – Career Advice for Aspiring Pros
41:15 – The Power of Mentorship & Community

πŸ”— Resources & Links: