Chasing Entropy Podcast 017: The Storyteller’s Journey with Bill Brenner

In this episode of Chasing Entropy, Dave Lewis sits down with longtime friend and industry veteran Bill Brenner, Senior VP and Head of Content at Cyber Risk Alliance. Bill has been shaping the cybersecurity narrative for over two decades, from his early reporting days at TechTarget to his leadership roles at Akamai, Sophos, IANS, and now Cyber Risk Alliance.

From Newsrooms to Cybersecurity

Bill shares how his career began in traditional journalism, with a pivotal moment after 9/11 pushing him toward B2B reporting. A role at SearchSecurity marked his entry into cybersecurity, where he quickly established himself as a respected interviewer, writer, and—eventually—a storyteller within the security community.

The OCD Diaries & Mental Health Advocacy

A major part of Bill’s journey has been his candid writing in The OCD Diaries, a personal blog turned community resource. What started as a therapeutic exercise evolved into a touchstone for many in security facing similar struggles. Today, Bill continues that advocacy through his work with CyberMinds, developing tools and resources to support the mental health of cyber defenders, who often face burnout, PTSD-like stress, and relentless alert fatigue.

Storytelling, Security, and Leadership

Reflecting on his time at Akamai, Bill discusses how being embedded in a security team during the Heartbleed and Shellshock era shaped his understanding of communication, trust, and leadership. He and Dave revisit their collaboration on reports, vulnerability advisories, and how content can influence both internal teams and the wider industry.

AI, Content, and the Human Element

Bill and Dave dive into the current disruption caused by artificial intelligence. While many companies mistakenly see AI as a replacement for people, Bill argues it must be used as an enhancer—freeing humans from repetitive tasks while preserving creativity, critical thinking, and authenticity. His own work at Cyber Risk Alliance now includes experimenting with AI to streamline workflows without losing the human voice.

Looking Ahead

Bill emphasizes the importance of resilience, humility, and staying focused on the human side of security. Whether through mental health advocacy, building stronger content strategies, or mentoring the next generation, his mission remains clear: tell stories that matter and help the community thrive in an increasingly chaotic digital world.

👉 Where to find Bill:

• The OCD Diaries (archived blog with evergreen posts)
• Bill on LinkedIn (active writing and insights)
• SC Media / SC World (ongoing journalism and leadership work)