In this episode of The Phillip Wylie Show, Phillip Wylie sits down with legendary application security pioneer and entrepreneur Jeremiah Grossman to discuss the evolution of web security, vulnerability management, cyber insurance, AI-driven software development, and the future of offensive security.Jeremiah shares his hacker origin story, from hacking his ISP as a teenager to discovering vulnerabilities in Yahoo Mail during the early days of the web. That experience eventually led him to Yahoo and later to founding WhiteHat Security, one of the first SaaS-based web application security companies.The conversation dives deep into how application security evolved from manual testing and early vulnerability scanners into scalable AppSec programs, as well as why modern vulnerability management is still fundamentally broken. Jeremiah explains why only a tiny percentage of CVEs ever lead to real financial loss and how his latest company is approaching vulnerability prioritization differently.
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Connect with Jeremiah Grossman:
LinkedIn: https://www.linkedin.com/in/grossmanjeremiah
Website: https://www.jeremiahgrossman.com
Root Evidence: https://www.rootevidence.com
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Connect with your host, Phillip Wylie:
https://linkedin.com/in/phillipwylieX
https://x.com/PhillipWylieInstagram
https://www.instagram.com/phillipwylie
Chapters
00:00 Introduction to Content Creation Journey
02:15 Eva's Hacker Origin Story
05:03 Career Advice for Aspiring Cybersecurity Professionals
06:19 The Importance of Skills Over Certifications
07:44 Motivation Behind Content Creation
10:00 Navigating Misinformation in Cybersecurity Education
12:57 The Role of AI in Content Creation
13:41 Mindset Shifts for New Content Creators
16:38 Types of Content and Finding Your Niche
18:20 The Importance of Experience in Content Creation
20:41 Balancing Structure and Authenticity in Content
24:44 Equipment Recommendations for Beginners
28:18 Final Thoughts on Content Creation
31:44 Phillip Wylie Show Outro
