Pineapple Squared
Education.
Hospitality.
Transformation.
Pull Up a Chair
Jimmy Chalmers — Pineapple Squared
This Is Your Moment
You built things.
Now build what's next.
Decades of hard work, real experience, and hard-won wisdom aren't liabilities in the age of AI. They're exactly what makes you unstoppable. Pineapple Squared was built to prove it.
Pineapple Squared — Built for You
Before We Begin
You already have
everything that matters.
Before you learned a single thing about AI — before you typed your first prompt — you already had the four things that matter most in the age of artificial intelligence. Sam Altman, CEO of OpenAI, named them himself.
Resilience
You've kept going when everything fell apart. More than once.
Adaptability
You've changed direction without losing who you are. That's rare.
Creativity
You see connections nobody else sees. Decades of living gave you that.
Anticipating Needs
You know what's needed before anyone asks. You've always known.
The Fifth Trait — The One That Unlocks All the Others
Insatiable Curiosity.
The refusal to stop asking why. The willingness to look foolish in pursuit of understanding. You had it at five years old. Some of you still have it. Every single one of you can get it back. That's why you're here.
Sources: The four core traits are attributed to Sam Altman, CEO of OpenAI — The OpenAI Podcast, Episode 1, timestamp 39:26. The fifth trait — Insatiable Curiosity — is a Pineapple Squared original. We cite our sources. Always.

The wisdom you've earned over a lifetime isn't a disadvantage in the age of AI — it's your greatest asset. We're here to prove it.

01
Education
Practical, hands-on AI training built for people with experience — not engineers. We translate technology into tools you already know how to use.
02
Hospitality
Every seminar, workshop, and training is a gathering, not a lecture. We pull up a chair. We make room at the table. Nobody leaves as a stranger.
03
Transformation
People don't leave with information — they leave changed. Equipped. Confident. Ready to lead into what's next instead of being left behind by it.
Our Purpose
To unlock the full potential of experienced Americans in a world being reshaped by technology.
Our Mission
Through education, hospitality, and transformation, we equip those overlooked by the AI revolution to lead — not follow — into what's next.
What We Do
The Workshop Train Coach Consult Speak Gathering

We gather people at the table where wisdom meets what's next.

Who We Serve
Churches & Ministry
Pastors, staff, and congregations ready to multiply their impact
🔧
Trades & Blue Collar
Construction, contractors, and skilled workers with decades of expertise
🏪
Small Business
Owners and operators ready to compete smarter, not harder
🏥
Healthcare & Caregivers
Professionals navigating a rapidly changing field
🎓
Educators & Nonprofits
Organizations serving communities with limited tech resources
👷
First-Generation Professionals
People who built careers with their hands and are ready to build what's next
Why We Exist
Only 18% of employed Americans over 50 have ever used AI at work — not because they lack capability, but because nobody built a seat for them at the table. And 81% of adults 50 and older say they want to learn more. The desire is there. Pineapple Squared is the door.
Sources: Pew Research Center, February–March 2025  |  University of Michigan National Poll on Healthy Aging, February 2025
Real People. Real Results.
Read What People Are Saying →