Chris LaBossiereBUSINESS · COMMUNITY · LIFEKayYour executive assistant

Personal AI · I’m the first user

Kay. A lifetime of context. A little more room for life.

I run a company, chair a charity board, and try to be a decent husband, father and grandfather. All of it matters. Not all of it gets my attention. Kay is my AI executive assistant, there so the important things stop losing to the loud ones.

I talk to her, out loud, and she talks back. She knows the people, the history and the promises across my whole life. She tells me what needs me, prepares the work, and waits for my say-so before anything goes out in my name.

An old standard of trust, kept.

A painted portrait of Kay, my AI executive assistant
Kay is a painted AI character, not a historical photograph.

Why “Kay”

Kay Summersby drove an ambulance through the Blitz, then served as General Eisenhower’s driver, secretary and trusted aide from 1942 to 1945. As president of the Juno Beach Centre Association I spend a lot of time with that generation’s stories. She had the full picture, used good judgement and did whatever it took to help. That is the job I want Kay to do. Read her story

Kay and KayEA™

Kay is who I talk to. KayEA™ is the private AI system she runs on, on hardware I own, in my case a Mac Studio, with a backup at home and a copy kept safely off site. My context stays mine, whichever AI models do the work.

Building in public, carefully

I’ll share what works and what doesn’t. Public information lives on this site. Private records stay in KayEA, on my own hardware. Illustrations show the direction; they don’t claim a capability is live.

There is no public chat with Kay on this website, and it has no connection to my private records.

Meet Kay’s specialists

Kay runs the house.
These are the people she calls on.

Painted portrait of Kay

Kay

Your executive assistant

Holds the whole picture, decides who does what, and checks the work before it reaches me.

Works for me. Everyone else works for Kay.

Painted portrait of Pippa

Pippa

Keeper of the vault

Runs everything inside the vault. Keeps every record safe, sorted and current, and keeps every specialist doing their part.

Reports straight to Kay, and does whatever Kay asks.

Painted portrait of Specs

Specs

Engineering director

Decides what gets built next and in what order, and keeps the lead engineers for the website, the product and the servers working as one team.

Reports to Kay, and brings the big decisions and blockers to me.

The specialists
Painted portrait of Porter

Porter

The front door

Greets people who want to reach me, and brings me only what’s worth my time.

Painted portrait of Booker

Booker

Finance

Keeps the books, bills and budgets straight.

Painted portrait of Butch

Butch

Publicist

Press, announcements, and how the story gets told.

Painted portrait of Sparks

Sparks

Social & comms

Social media, newsletters and every message going out.

Painted portrait of Keyes

Keyes

Security

Guards accounts and access, and decides who gets the keys to what.

Painted portrait of Scout

Scout

Research & listening

Reads widely, hears what’s being said, and reports back.

Painted portrait of Dottie

Dottie

Calendar & travel

Keeps the days, trips and tickets in order.

Painted portrait of Belle

Belle

Household

Runs the whole house: home automation, alarms and monitoring, the pantry, recipes, and everything the home needs.

Painted portrait of Rivets

Rivets

The engineering crew

Lead engineers who can turn a hand to anything: they build, ship, host and maintain everything digital. They report to Specs.

Painted portrait of Sketch

Sketch

Product design & creative

Creative director. Shapes how every product, page and painting looks and feels, so it all belongs to one world.

Painted portrait of Parker

Parker

Legal & contracts

Reads the fine print, keeps the agreements, and makes sure nothing gets signed without a second look. Somebody has to read the terms and conditions. It’s me. Happily.

Painted portrait of Pep

Pep

Health & wellbeing

Workouts, appointments, sleep and the nudges that keep me in shape for everything else.

Painted: Pippa, keeper of the vault, among long aisles of recordsInside the vault. Pippa answers to Kay and keeps every record, and every specialist, in order.

The cast are painted characters in the style of the KayEA film. Belle first joined the team at Barney’s Tavern.

Kay and her specialists keep this house running. Meet the cast →