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