Meet Leo
The AI Jimmy Built
Pineapple Squared
Education.
Hospitality.
Transformation. pineapplesquared.io
The Question That Started Everything
What if AI could give you back
two hours every week?
Not two hours of screen time. Two hours of your life — back in your hands. That's what we're here to show you how to do.
June 27, 2026 · Woodstock, GA
First Gathering at Rally Point Grille — 12 seats. Come for an hour. Leave different. Reserve your seat →
Blue collar worker with laptop and notepad

You built things.
Now build what's next.

Fifty years of trades, pulpits, and job sites taught us one thing: experience isn't a liability. It's your biggest advantage — and AI is how you put it to work.

Jimmy Chalmers — Founder, Pineapple Squared

You're not behind. You're exactly where you need to be — and there's a seat at the table with your name on it.

Education

Hands-on learning built for people who've been doing things the hard way their whole lives. No jargon. No condescension. Just tools that work.

Hospitality

Pull up a chair. This isn't a cold classroom or a corporate training room. Every session feels like a conversation at a good table.

Transformation

You leave different than you arrived. Not just with new tools — with new confidence in what's possible for you and your work.

What We Do
The Workshop
From Stranger to Sidekick
Half a day. Six real AI tools you build yourself. This is the clearest on-ramp we've found — for anyone ready to stop watching from the sidelines and start doing. Whether you're by yourself or bringing your whole crew, this is where it starts.
See what's included
Train
Your team. Your turf.
Group training for your crew, congregation, or organization. We bring the tools, the stories, and the patience. You keep the results — and a team that can actually use what they learned.
Start the conversation
Coach
One chair, one conversation.
Your schedule, your questions, your specific situation. This isn't a class — it's a conversation built around where you actually are and where you actually want to go.
Let's talk
Consult
Strategy for the long game.
For businesses, churches, and organizations ready to build AI into how they operate. We assess where you are, advise where to go, and help you implement. No one-size-fits-all playbook.
Talk strategy
Speak
Jimmy in your room.
Rotary clubs, trade associations, conferences, Sunday school classes, pulpits, ladies' garden clubs. The Blue Collar Renaissance is here — and your people need to hear why it matters for them.
Book Jimmy
Gathering
Not a conference. A conversation.
Sometimes a pint at a brewery. Sometimes three days in the mountains. Same spirit either way — honest talk about what AI means for people like us. First one: June 27, 2026 in the Atlanta area.
Find out more
Why This Matters Right Now
18%
Of employed Americans over 50 have used AI at work — less than half the rate of workers under 30. Not because they can't. Because nobody built the right on-ramp.
Pew Research Center, June 2025 (confirmed March 2026)
58%
Of adults 50 and older want to know more about what AI can do for them. The desire is there. The starting point built for their experience level — that's what's been missing.
University of Michigan National Poll on Healthy Aging, February 2025
Who Thrives in the AI Era
Sam Altman, CEO of OpenAI, says the people who will do best with AI share four traits. We added a fifth.
1
Resilience They've been knocked down before. They get back up. Sound familiar?
2
Adaptability They've learned new tools on the fly their whole careers. AI is one more.
3
Creativity They solve problems every day that weren't in any manual. That's creativity.
4
Anticipating Needs They read the room. They see what's coming. They act before they're asked.
5
Insatiable Curiosity Jimmy's addition. The ones who lean in, keep asking, and never stop learning — those are the ones who win.
Source: OpenAI Podcast, Episode 1 — timestamp 39:26. Trait 5 added by Jimmy Chalmers.
Our Purpose
Pineapple Squared exists to help the people who built this country — with their hands, their faith, and their grit — find their footing in an AI world before it passes them by. Experience is your advantage. We're here to help you use it.
About Jimmy
Jimmy Chalmers — Founder, Pineapple Squared

I spent decades in construction and have stood behind more pulpits than I can count. I work a Pro Desk at Home Depot, run a black car service with my wife Victoria, and I'm proud to call Woodbine Station home. I'm also passionate about what God is doing through Mission Church on Roswell Street in Marietta.

For years I owned and operated Front Porch Apiary in North Carolina. I've loved honeybees my whole life. There's something about standing in the middle of hundreds of thousands of buzzing bees that puts me closer to God than any cathedral ever has.

I'm not a tech guy. I'm not from Silicon Valley. I built this website with the help of AI — learned every step as I went, no coding background, no tech degree. I run five different AI models every day. I spent months building Leo, my personal AI aide-de-camp, from scratch — his operating constitution runs twelve pages. I've learned things I didn't know I could learn and built things I didn't know I could build.

Just stubbornness, curiosity, and tools that didn't exist a few years ago.

That's when I knew this wasn't just for young people in hoodies. If I could do it, so could you. And now I can show you how.

Experience isn't a liability in the age of AI. It's your biggest advantage. I'm here to prove it.
Read: The Constellation Brain →

Real People. Real Results.

Read Their Stories