Dan DeCloss: The Evolution of Cybersecurity episode artwork

EPISODE · Jun 11, 2025 · 37 MIN

Dan DeCloss: The Evolution of Cybersecurity

from Phillip Wylie Show · host Phillip Wylie

SummaryIn this episode of the Phillip Wylie Show, host Phillip Wylie speaks with Dan DeCloss, founder of PlexTrac, about his journey in cybersecurity, the evolution of pen testing, and the challenges faced in the industry. Dan shares his hacker origin story, insights on recruiting talent, and the inspiration behind PlexTrac, a tool designed to streamline the pen testing reporting process. They discuss the future of cybersecurity, including the role of AI and the importance of community engagement in recruiting talent.Takeaways• Dan DeCloss has over 20 years of experience in cybersecurity.• PlexTrac aims to simplify the pen testing reporting process.• Networking is crucial for breaking into cybersecurity.• BSides events are great for recruiting talent.• The cybersecurity landscape has evolved significantly over the years.• AI is becoming increasingly important in cybersecurity tools.• Pen testing is not just about finding vulnerabilities but also about effective reporting.• Community engagement is vital for talent acquisition in cybersecurity.• PlexTrac was inspired by the challenges of report writing in pen testing.• The future of PlexTrac includes enhanced features and AI integration.Sound Bites"I feel like we truly helped the industry.""AI is going to help our customers.""We do have a free trial."Chapters00:00 Introduction to PlexTrac and Dan DeCloss03:01 Dan's Hacker Origin Story07:19 Evolution of Cybersecurity and Pen Testing13:39 Types of Pen Testing and Experience16:31 Advice for Aspiring Pen Testers20:33 Recruiting Talent in Cybersecurity23:13 Inspiration Behind PlexTrac30:10 Future Roadmap for PlexTracResourceshttps://www.linkedin.com/in/ddecloss/https://www.linkedin.com/company/plextrac/Try PlexTrac Core for Free

SummaryIn this episode of the Phillip Wylie Show, host Phillip Wylie speaks with Dan DeCloss, founder of PlexTrac, about his journey in cybersecurity, the evolution of pen testing, and the challenges faced in the industry. Dan shares his hacker origin story, insights on recruiting talent, and the inspiration behind PlexTrac, a tool designed to streamline the pen testing reporting process. They discuss the future of cybersecurity, including the role of AI and the importance of community engagement in recruiting talent.Takeaways• Dan DeCloss has over 20 years of experience in cybersecurity.• PlexTrac aims to simplify the pen testing reporting process.• Networking is crucial for breaking into cybersecurity.• BSides events are great for recruiting talent.• The cybersecurity landscape has evolved significantly over the years.• AI is becoming increasingly important in cybersecurity tools.• Pen testing is not just about finding vulnerabilities but also about effective reporting.• Community engagement is vital for talent acquisition in cybersecurity.• PlexTrac was inspired by the challenges of report writing in pen testing.• The future of PlexTrac includes enhanced features and AI integration.Sound Bites"I feel like we truly helped the industry.""AI is going to help our customers.""We do have a free trial."Chapters00:00 Introduction to PlexTrac and Dan DeCloss03:01 Dan's Hacker Origin Story07:19 Evolution of Cybersecurity and Pen Testing13:39 Types of Pen Testing and Experience16:31 Advice for Aspiring Pen Testers20:33 Recruiting Talent in Cybersecurity23:13 Inspiration Behind PlexTrac30:10 Future Roadmap for PlexTracResourceshttps://www.linkedin.com/in/ddecloss/https://www.linkedin.com/company/plextrac/Try PlexTrac Core for Free

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This episode was published on June 11, 2025.

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SummaryIn this episode of the Phillip Wylie Show, host Phillip Wylie speaks with Dan DeCloss, founder of PlexTrac, about his journey in cybersecurity, the evolution of pen testing, and the challenges faced in the industry. Dan shares his hacker...

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