Podcast: Adventures of Alice & Bob

Charles Herring 23 April 2026
Alice and Bob Podcast with Charles Herring
In this episode, James talks to Charles Herring about what happens when an IT wizard runs away to join the Navy, works on fighter jets, and then gets thrown into cybersecurity right after 9/11? He shares his unconventional journey from the Wild West days of network defense, complete with fighting worms with worms—to being CISO during the Target breach. Plus: why trauma creates silos, why your SOC is like throwing receipts in garbage bags, and what it takes to build a "good neighborhood" in cybersecurity.

Lost in Space, Time and Standards

Charles Herring 16 March 2026
Southern Cross
I anticipated most of the challenges of moving to New Zealand. Immigration, housing, saying goodbyes. What I didn't anticipate was how exhausting it would be to relearn space, time and standards. When seasons run backwards, Mondays happen twice, and you find yourself whispering 'I miss inches' in bed, the cumulative toll is real. Fortunately, wonder makes a good coping mechanism

Supersonic Broken Processes: The Hazards of Automating Cybersecurity with AI

Charles Herring 15 March 2026
Speedometer
You cannot accelerate a process to supersonic speeds if it barely works at five miles per hour. Applying Anthropic's 4D Framework for AI Fluency to cybersecurity automation reveals that all four D's (Delegation, Description, Discernment, Diligence) fail when built on the same siloed, philosophy-free foundations that have plagued SECOPS for decades. The consequences in our field are uniquely severe: the AI can't go to prison when it gets it wrong.

How AI was the Best Bender of My Life

Charles Herring 11 March 2026
Lake Tekapo
I built guardrails for the code, the architecture, and the security. I forgot to build guardrails for myself. After an eight-month megasprint rebuilding 10 years of work with Claude, I ended up on bedrest for a week. Turns out AI-assisted development is the most potent productivity drug ever created, and the dose that makes it medicine and the dose that makes it poison are closer together than you'd think.

Why I'm Not Losing Sleep Over AI Stealing My Job or My Soul

Charles Herring 10 February 2026
A Tunnel to Light
After six months of building WitFoo's analytics platform with Claude Code, I'm more convinced than ever that AI coding tools make experienced practitioners more valuable, not less. Claude is an extraordinary Warrior, but the Wizard's strategic vision, the Poet's search for meaning, and the hard-won knowledge of the WitFoo Way remain stubbornly, irreducibly human. The Foo has been upgraded. The Wit remains ours.

New Zealand Move Notes

Charles Herring 2 November 2025
Charles in Russel New Zealand

Background

Over the course of a year from November 2025 to November 2026, Mai and I researched and eventually moved to New Zealand. We were looking for a life change and my work at WitFoo needed to plan for international expansion. My extensive notes are found below. 

Advisors

Our move was made much easier by a few advisors. I am pretty good at paperwork and research and thought of doing it myself to save some money. I ended up feeling that all 3 of these advisors over delivered on value and made our move much more successful.

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