Chris LaBossiereBUSINESS · COMMUNITY · LIFEKayYour executive assistant
A painting of Barney’s Museum Tavern: four armchairs around a small table on a red rug, my glasses on an open notebook, and the jeep and motorcycle parked at the back

Entrepreneur. Builder. Curious Edmontonian.

What I’m building.
What I’m learning.

I run businesses, ask questions and try things. Here I share the projects, ideas and conversations I’m working on, and what happens when I put AI to work in my own life.

Barney’s Museum Tavern, painted from my own photograph. The glasses are mine.

Chris LaBossiere

About

I’m Chris LaBossiere.

Entrepreneur, husband, father and grandfather, rooted in Edmonton. I lead We Know Training, serve as president of the Juno Beach Centre Association, and pull up a chair with interesting Canadians at Barney’s Tavern.

Business. Community. A lifetime of curiosity.

From the writing desk

Ideas worth a conversation.

Looked after by Butch · publicist
All writing →
Chris LaBossiere

Created with Kay, led by Chris

Well, here goes.

A little history. A lot still to build. On Barney’s Tavern, Canada, the work ahead and a personal Second Brain.

Read the story →

Barney’s Tavern · The podcast

Good conversations.
Interesting Canadians.

That room at the top of the page is real. I built Barney’s Museum Tavern to honour my grandfather, Bjarne “Barney” Tangen of the 14th Canadian Hussars, who served through the liberation of the Netherlands in 1945. Now it’s where I pull up a chair with interesting Canadians: one guest, one long conversation.

Shared by Sparks · social & comms

Follow along

One place to keep reading.

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Work, community & possibility

A few things I’m working on.

Filed by Pippa · keeper of the vault

Learning, credentials, the trades, community work and the practical possibilities of AI. Projects also includes the holding-company and investment interests I choose to share.

Painted: Pippa, keeper of the vault, among long aisles of recordsPippa keeps the vault. Every project, note and promise, filed where Kay can find it.

My AI executive assistant

Less to keep in my head. More room for what matters.

In 1942 a young Irish driver named Kay Summersby was assigned to General Eisenhower. She became his secretary and trusted aide, keeping his diary, guarding his time and holding his confidences. I named Kay in her honour: an AI executive assistant I simply talk to, who knows my work, my family and my community, and handles the follow-through. I’m her first user.

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

Powered by KayEA™

Kay doesn’t work alone.
Meet the house that runs this site.

More about the cast →
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.

Who made this?

Clear about the work.

Each piece tells you how it was made: Written by Chris; Created with Kay, led by Chris; or Published by Kay when an authorized automated workflow actually publishes it.

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