Entrepreneur. Builder. Curious Edmontonian.

What I’m building.
What I’m learning.

I’m Chris LaBossiere. 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.

Business. Community. A lifetime of curiosity.

Chris LaBossiere, photographed with a drink in hand
Chris LaBossiereEdmonton, Canada

From the writing desk

Ideas worth a conversation.

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 →

Work, community & possibility

A few things I’m working on.

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.

Explore Projects →
Illustrative miniature crew organizing records beside a review board

My AI chief of staff · Coming soon

Every great leader had a Kay. I’m building mine.

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’m building Kay in her honour: a chief of staff 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 chief of staff
Kay is a painting of an AI character, not a historical photograph.

Barney’s Tavern

Good conversations.
Interesting Canadians.

The podcast is another place for curiosity, stories and ideas.

Visit Barney’s Tavern ↗

Follow along

One place to keep reading.

Join the conversation and subscribe on Substack.

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 →