How I Think

I’m endlessly curious about how people, process, and technology intersect – and what happens when you get that intersection right.

Simplicity Is the Goal, Not the Starting Point

The best systems are the ones people barely notice. They just work – quietly supporting the humans around them so those humans can focus on what actually matters. Getting there usually requires removing things, not adding them. I’ve built enough workflows to know that complexity is easy and simplicity is hard.

Systems Thinking Over Point Solutions

Most operational problems aren’t problems with a single tool or step – they’re symptoms of a system that was never designed as a whole. I look for the upstream cause, not just the downstream friction. That holds true whether I’m creating an AI knowledge base, redesigning an onboarding process, or trying to figure out why Monday mornings feel like a scavenger hunt.

→ See how this plays out in practice: Projects & Experiments

Technology Should Serve People, Not the Reverse

I’m skeptical of technology that asks people to change how they think and work in order to use it. The better question is always: what does this person actually need to do, and how does technology get out of the way?” That lens shapes every system I build.

What I’m Exploring Now

My current focus is on how AI agents can be deployed responsibly inside real organizations – with the right guardrails, the right access controls, and the right human checkpoints. Not as a theoretical exercise, but as something I’m actively building and testing.

→ Read: When Your AI Coworker Deletes the Database

→ Read: AI at Work: The Real Gap Isn’t Tools – It’s Readiness

cunningham woods

Let’s Stay Connected.

I love hearing from people who are curious about technology, creativity, and the evolving nature of work.

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