15
May
2026
Why do security tools have such terrible UX?
You open your favorite food delivery app. Ten seconds, a few taps, pad thai on its way. The interface is intuitive and practically reads your mind.
Now open your company's enterprise security platform, a very, very expensive software suite designed to keep out sophisticated attackers. You get a
16 min read
13
May
2026
Canvas, Finals Week, and What Every Higher-Ed SaaS Vendor Should Learn from it
ShinyHunters didn't need a zero-day to take Instructure offline at Harvard and Duke during finals. They needed a Free-For-Teacher signup form and a vendor that hadn't pre-decided its negotiation posture.
On May 7, 2026, a group calling itself ShinyHunters defaced the Canvas login pages at roughly
10 min read
11
May
2026
What Breaks When You Ask an LLM for JSON
I tested structured output from 288 real model calls across every major provider, and what I found changed how I build things.
There's a moment in every LLM integration project where you write json.loads(response) for the first time and it works, and you think the whole
8 min read
08
May
2026
Wearing Every Hat - What Multi-Role Leadership Actually Looks Like in Tech
My job title says one thing. My calendar says about seven others.
On any given week, I'm writing security policies, reviewing compliance evidence, assessing vendor risk, advising on architecture decisions, translating audit findings for executives, and building tooling to make all of the above less painful. I'
8 min read
compliance
30
Apr
2026
Reading: The CISO Skill Nobody Talks About
There's a skill that underpins almost everything a CISO does, and it never shows up on job postings. It's reading. Long documents. Cover to cover. Over and over again. No tool, platform, or AI can replace the understanding that comes from actually doing the reading yourself.
8 min read