About
I've spent 25+ years in the middle of major technology shifts. Not the slide deck version — the part where you actually have to make it work.
Across roles at Microsoft and Stripe, I built platforms that are still running: Microsoft Learn, Microsoft Docs, Stripe Docs. Developer experience, documentation, operating models — the kind that keep working after the team that built them has moved on. The pattern is always the same: big strategy meets messy reality, and someone has to close the gap. That's always been the work.
Right now, that gap is AI. And — turns out — it's also worldbuilding, wearables, and tabletop campaigns. Same instinct, more surfaces.
What I'm building
Obaron — AI Readiness auditor for developer docs. Lightning Scan free, $49 deep audit, MCP-native so it runs from Claude. Shipped in four days. The number is real and it has context: a year of prior prototyping, AI-native workflows I've been refining longer than that, and 25 years of knowing what a shippable thing looks like.
Cocoajam — a platform turning tabletop RPG sessions into web series. The TTRPG community already tells the best stories. They deserve better tools to share them.
A fantasy series — magic system grounded in pseudo-physics (components + speech + will), three villain archetypes, three protagonists orbiting at different social layers. Art books and a web series planned.
What else I make
Generative art that looks illustrated. Candid photographs of things most people walk past. Clothes designed from my own photos and illustrations. Short videos about absurd everyday observations.
The Flash and Silverlight kid never went away. AI gave that hybrid designer-engineer identity a second act.
Greatest Hits
- Obaron — AI Readiness auditor for developer docs. You put in your domain, get your AI Readiness Score and a report of exactly what's blocking AI agents from finding your content. Shipped in four days.
- Stripe Docs — helped upgrade the documentation platform for one of the most developer-loved APIs on the planet
- Microsoft Learn — scaled Microsoft's developer learning platform to millions of monthly users
- Microsoft Docs — helped move all of Microsoft's technical documentation from MSDN to the open web
- Xbox Apps — shipped apps on the console people actually played games on
- Windows Phone Apps — shipped apps on the console people... didn't
- Silverlight — the browser plugin era, in all its glory
- MIX Conference — Microsoft's web and design conference which was too cool to continue
- Channel 9 — developer video community before YouTube ate everything
- Unreal Tournament — yes, that one. Made maps. Fragged people. No regrets. Bombing Run!
- Formula Boats — built the website for a company that built actual boats. With fiberglass. The original "shipping"
- US Army — where I learned that systems thinking isn't optional
The pattern: platform work. Not features — the layer that features run on. The platforms now just include worlds and wardrobes.
Let's Talk
If you're the one who has to make the AI strategy actually work — or you run a TTRPG group with stories worth filming, or you just want to trade workflows — reach out.