Articles

Articles on AI, coaching, product strategy, and building a business that matters.

1623 posts

The Key Comes Before the Song

aiMay 22, 2026

When you build with AI doing the content generation, the obvious move is QA at the end. But if that's your whole strategy, you sat down at the piano without picking a key. Here's how I'm thinking about evals for a new product — and why guardrails belong upstream, not downstream.

aiproduct-work

Use Claude to get you questions, not answers

aiMay 20, 2026

Most Claude sessions produce transcripts because users ask for answers. The posture that produces real specifications looks different. Here's what it requires.

ai

Stop Selling a Privacy Policy

aiMay 18, 2026

When both sides have IP, current AI privacy answers force one of them to bleed. The fix isn't a better policy or a clever cryptographic trick. It's a design discipline: stop protecting what crosses the wire and start designing what's allowed to cross in the first place.

aiinsightsproduct-work

You don't have to be technical to own the architecture

aiMay 16, 2026

AI is changing everything and nothing at the same time. So where should you spend your scarce time? Three things will always matter: your domain, systems thinking, and architecture. And architecture isn't what most people think it is. It's the load-bearing decisions you care about, written down before the AI builds the wrong thing.

aiproduct-work

The 4 scans I run before I'm done with any AI-assisted project

aiMay 14, 2026

There are no magic prompts. But there are four scans I run after every first pass on AI-assisted code: race conditions, concurrency, idempotency, and dead code. Each one catches issues you'd otherwise debug months later.

aiproduct-work

Lovable, and the cardboard model problem

product-workMay 12, 2026

Most people who have ideas aren't developers, so their ideas live and die in one head. Lovable changes the cost of building a cardboard model to roughly zero. Here's what that means for the conversations you can finally have.

product-workai

The harness is the craft.

aiMay 10, 2026

Most engineers pick a model they trust, eyeball a couple of runs, and ship. I don't ship that way. Here's what eval-driven development actually looks like, and the seven principles I'd hand to anyone shipping LLM systems.

aiproduct-work

What Is a Claude Skill? Let's Look Closely at One.

aiMay 8, 2026

A Claude Skill teaches AI to work the way you want, not the average way. Here's a walkthrough of one I built (Expert Profiler) and the install pattern you can reuse for any technical setup.

ai

Why Your AI Bill Is Too High (And the Architecture Fix That Saves 40%)

aiMay 6, 2026

Most companies run their AI like a doctor's office. The ones that scale run it like an ER. Here's the architecture decision that cuts AI costs by 40%.

aiproduct-workinsights

The CRM I built this weekend doesn't have a UI. Agentic Software is the future.

aiMay 4, 2026

I built a CRM this weekend with no UI. Just tools an AI agent can call. Here's why agentic software is the next decade of building.

aiproduct-workinsights

Want to talk about what you just read?

Every great conversation starts with a single question.