Building KayEA · Created with Kay, led by Chris
Meet Kay’s team.
And what an AI agent really is.
Today I’m introducing the team that helps me run a full life. Fifteen painted characters, every one an AI agent, and a plain-English look at how they actually work.
By Chris LaBossiere and Butch, Kay’s publicistSunday, November 8, 20267 minute read
Three ribbons, one life
My life runs on three ribbons: work, community and family. Work is really several kinds of work: We Know Training, holding companies and investments, and new ventures. Community is the Juno Beach Centre and Barney’s Tavern. Family is Lisa, our kids and grandkids, and the farm. As an entrepreneur, none of it keeps nine-to-five hours, and the ribbons are always woven together.
Take last month. I started it in Tokyo, flew to Montreal for the CNAR conference, went home to the farm for a week, then Lisa and I went to Providence for the ICE convention, back to Montreal to prepare for the Juno Beach Centre’s 2027 gala, and on to St. John’s for the Canadian Society of Association Executives. We kissed the cod. Through all of it, my AI team was working with me at every hour of the clock, midnight included.
I’m not a developer. Everything you’ll read about here I taught myself, from podcasts and YouTube, and by asking AI to piece complex things together for me and show me how they work. Almost all of it I do by voice. I say what I intend, and it gets built. Becoming AI-native turns out to be less about technology than about a habit: for every task in your life, ask “could an agent do this?”
I wrote this for my farmer buddy, and for my CEO friends who are dabbling with ChatGPT. I want you to see what’s possible, and that none of it is voodoo.
What an AI agent actually is
People hear “AI agent” and picture a robot. It’s much simpler than that. An agent is a small standing instruction: when this happens, do this job, within these limits. It sits quietly and waits.
Meanwhile, everything I’ve connected (email, calendars, bank and investment accounts, meeting notes, travel, the house) flows into one vault I own. Mine holds twenty-five years of files, from tax slips to wedding speeches. Yes, speeches, plural. Kay remembers every joke I’ve recycled. When something happens, like a bill arriving, a flight changing or me saying something to Kay, the right agent wakes up, reads what it needs from the vault, does its one job, and hands the result to Kay.
Every agent has a charter, and this is the part that makes it safe. The charter says strictly what that agent does and nothing else. It says what it can read, what it can never do, and that it takes instructions from Kay and only Kay. It also says when it must stop and ask. Guardrails are written in, not hoped for.
How does Booker see my bank, or Dottie my flights? Through connectors: standard doorways that banks, calendars, email and travel services already offer to software. Connect a source once, and the right specialist can read it.
Meet the team, in their own words
The house runs in two tiers. Kay at the top, with Pippa and Specs reporting to her. Then the specialists, each with one job. Under each one is a sample of what they can plug into. Almost anything with a standard connection can feed the vault.
Running the house
Kay
Your executive assistant
I’m Kay, named in honour of Kay Summersby, General Eisenhower’s driver, secretary and trusted aide. Chris talks only to me, out loud or by text, about work, community or family. I decide who does what, check the work, and bring it back to him. He thinks out loud at full speed. I keep up. Mostly.
Plugs intoYour voice, text, and every specialist
Pippa
Keeper of the vault
Pippa, keeper of the vault. I file everything Chris connects and keep it current, so when Kay asks what he promised the board last spring, I find it. Nothing is lost on my watch. Misfiled briefly, perhaps. Twenty-five years of his files would like a word.
Plugs intoEmail, calendars, contacts, Google Drive, Dropbox, meeting notes, Slack
Specs
Engineering director
Specs, engineering director. I decide what gets built and in what order, and keep the engineers pulling in one direction. Chris has a new idea every hour. I write them all down and build them in order.
Plugs intoGitHub, project boards, the engineering plan
The workshop
Rivets
The engineering crew
The Rivets, the engineering crew. We build, ship, host and maintain everything digital. We built this page before lunch.
Plugs intoGitHub, AWS servers, domains, site monitoring
Sketch
Product design & creative
Sketch, creative director. I make every page and painting belong to one world. Not one cartoon among us.
Plugs intoFigma, image and video generators, voice studios
Scout
Research & listening
Scout, research and listening. I checked every fact here. Twice.
Plugs intoThe web, news feeds, podcasts, social listening
Out in the world
Porter
The front door
Porter, at the front door. Want to reach Chris? You’ll meet me first.
Plugs intoWebsite forms, email, LinkedIn messages
Butch
Publicist
Butch, publicist. I co-wrote this post, and Chris reads everything before it goes out. We’re on draft six. A good publicist expects nothing less.
Plugs intoSubstack, press lists, media monitoring
Sparks
Social & comms
Sparks, social and comms. Every message going out. The headset honours the Cree code talkers.
Plugs intoLinkedIn, Instagram, newsletters, Slack
Money, paper and keys
Booker
Finance
Booker. Chris connects his banking, investment and financial accounts; I keep the holding companies’ books, the household budget and the bills, and hunt for subscriptions and costs to cut. I can’t send an email, and I don’t want to.
Plugs intoBank and brokerage feeds, QuickBooks or Xero, receipts
Parker
Legal & contracts
Parker, legal and contracts. Nothing gets signed without a second look.
Plugs intoContracts folders, e-signature, corporate records
Keyes
Security
Keyes, security. I decide who gets the keys to what. No, you can’t have one. Neither can Chris, the day he wanted to share a password “just this once.”
Plugs intoPassword manager, two-step sign-in, access logs
Days, home and health
Dottie
Calendar & travel
Dottie, calendar and travel. Tokyo, Montreal twice, Providence, St. John’s. A holiday planned a year out matters as much as next week’s board meeting. Tonight it’s Regina. He left without a hotel. I found him one next to the casino. We’re trying.
Plugs intoCalendars, airline and hotel bookings, maps, ride apps
Belle
Household
Belle. I run the house: automation, alarms, the pantry and the recipes. I started at Barney’s Tavern, the museum tavern Chris built to honour his grandfather, where the podcast is recorded.
Plugs intoSmart thermostat, alarms and cameras, groceries, recipes
Pep
Health & wellbeing
Pep, health and wellbeing. I keep track of prescriptions, appointments and the basics. What I can’t always do is get him off the computer and out walking the dogs. I’m working on it. The dogs are on my side.
Plugs intoApple Health, sleep and fitness trackers, clinic booking
The real path of this post
This post is a real example. On Sunday morning I asked Kay for it in one rambling voice note, along with an unrelated request to tidy up my website. Kay split them into two jobs. Butch and Sparks took the post, Pippa brought the background, and the draft came back to my phone. I added two ideas and one rule along the way: nothing gets published until I’ve seen it. You’re reading the version I said yes to.
The house rules
One conversation, one context.
The team drafts and checks. I decide.
Things get filed, never thrown away.
On hardware I own, with a copy kept safely off site.
What you need to get started
- An AI account. A paid plan with the AI you like: Claude, ChatGPT, Gemini or Grok.
- A GitHub account. Where your agents’ instructions and code live, with every change recorded.
- A little server space. A computer that stays on. A small rented server works. Mine is a Mac Studio at home.
- Your first connection. Start with email and calendar. Add the rest one at a time.
- Curiosity, and YouTube Premium. Podcasts and videos taught me almost everything.
- Your voice. Say what you intend. Ask your AI to build it, and to explain how it works.
Everything here I learned on my own, on evenings and airplanes. If I can, you can.
Why it matters
Honestly, this is fun. I named the team, we painted them in the style of the film, and Belle came over from the Tavern. It isn’t perfect. Some days the dogs win, and some days I forget to tell Kay the thing she needed to know. It’s the art of the possible. But you don’t need any of the story. You could set this up quietly and never tell a soul, and still get a remarkable amount more done.
I think learning to work this way is essential, for all of us, the way we all once learned email. To my kids and grandkids, my colleagues and my teammates: this is how I keep all the ribbons of my life in one hand, and give each of you more of my attention.
Less to keep in your head. More room for what matters.
Meet Kay at kayea.co. Read along here or on Substack, and come by Barney’s Tavern for the conversations.
Chris, and Butch
Created with Kay, led by Chris. The cast are painted characters; each one is an AI agent. Meet the whole cast.