I'm Jesse James Richard. I've spent more than twenty years building companies' software from the first line of code — four companies' worth. This site is where I write about how.

It started with a video game written in Pascal at a University of Calgary programming camp when I was twelve. The thing on the screen did what I told it to do, and that was it — hooked.

Passportal came first: co-founded around 2010, a password management and IT documentation platform for MSPs. I wrote all the software — the LAMP stack, the mail servers, the DNS, the integrations. It grew until SolarWinds acquired it.

Made Live was next: six years on an AI-assisted children's storybook publishing platform. It didn't survive contact with its market, and that tuition — everything about making AI-generated work trustworthy enough to publish under your own name — is baked into everything I've built since.

ManaJing after that: a Microsoft Sentinel management platform, full Azure stack, production. And now Giant Context — an AI marketing platform on GCP, and the first company where I do all of it: code, infrastructure, product, pricing, and the marketing copy that explains it.

The build log. Giant Context was built by one architect conducting a crew of AI agents, and this blog is the technical history of that build: the architecture decisions, the war stories with surprising root causes, the methodology that emerged from working this way, and the infrastructure underneath it all.

No product pitches. The interesting parts of building software are the parts that surprised you — those are the only parts worth writing down.

I live in Canada with my family. I play hockey, walk my dog a lot, read more than most people think is reasonable, and write almost as much as I code.

You can reach me at j@jessejamesrichard.com.