Personal AI / In development

KayOS™ &
Second Brain.

A lifetime of context.
Put to practical use.

I’m building a system to help me follow through across my whole life. I’m also its first user. The point is to find out what works by actually living with it—and share what I learn.

Portrait of Kay, my AI chief of staff
Kay · AI chief of staff
The KayOS™ project at KayEA.co ↗

Three parts, with different jobs.

Second Brain is the context: a personal information vault designed to hold my ideas, memories, records and the background to my decisions.

Kay is the assistant: my AI chief of staff, intended to work with the context I allow her to use.

KayOS™ is the operating system: the tools, permissions and coordination that bring the two together. The vault remains separate so my information can outlast any one assistant or tool.

01 / Capture

Bring the context together.

Thoughts, conversations, documents and memories I choose to keep.

02 / Connect

Give Kay useful context.

Let approved agents refer to the relevant parts of my personal record.

03 / Follow through

Turn context into action.

Develop useful prompts, coordination and automations around that context.

This is the direction of the initiative, not a list of services available on this website. The public site has no connection to my private vault and no live Kay chat.

My information, under my control.

By sovereign data, I mean keeping control over where my information lives, who can access it and which tools can use it. Encryption, reliable storage and clear permissions are requirements for the system I want to build.

One possibility starts with the Mac Studio sitting in Barney’s Tavern. I’m exploring how local hardware and securely hosted infrastructure could support a lifelong vault, with agents able to use approved context for reminders, research, data exchanges and automation.

I’m still designing and testing that hosting and security setup.

Being a better husband, father and grandfather matters as much as being a better CEO.

A project for the whole of my life.

I want this to help me show up more consistently: for my family, as a volunteer and community member, and for the people and businesses I lead. More useful context should mean better questions, better follow-through and fewer things slipping away.

Building it by using it.

I’ll share the experiments, the workflows and the things that don’t work. That includes how Kay helps research and produce writing, how I use agents around the house, and what I learn about keeping my information useful and under my control.

On published pieces, the byline will distinguish work produced by Kay, work we build together and work I write myself.

See the authorship guide →
The longer view: trusted people and “Virtual Grandpa”

Eventually, I’d like the front door to be a conversation with Kay. A colleague might explore how I would approach a question. My grandchildren might explore my stories through a “Virtual Grandpa.”

Each person’s access would be individually approved, limited to the context I choose, and revocable. An AI interpretation of me would be clearly identified as such; it would not be me or a perfect reproduction of my thinking.

Those are ambitions for the project. They are not features available here today.