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, 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 automation practice for SMBs and founders. The gap between "Claude exists" and "Claude is handling your intake and content work" is the whole job. That gap is what we close. Concierge service + scanner tools. First installs underway.
Cocoajam — the AI-native TTRPG platform. The DM and the Players stay the authors; Cocoajam runs the bookkeeping. Big Tech product-design rigor applied to tabletop. Encounter Manager in private beta.
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 and want tools that take it as seriously as you do, or you want to trade workflows — reach out.