Mapping how AI transforms companies, careers, and consulting. Built on direct experience deploying thousands of use cases.
Explore my work
About
I was a lawyer for one week. I read a book a day for a decade. I ran a marketing agency for ten years. My entire career has been in professional services, in the weeds, doing the work.
Then AI disrupted my business.
I didn't debate whether it was useful. I started using it. I embedded AI into our operations, figured out what worked, and started teaching other consultants how to do the same. Over the past two and a half years, we've trained hundreds of companies, deployed thousands of AI use cases, and delivered millions of dollars in documented productivity gains.
While most people are arguing on the internet about whether AI is ready for serious work, we are heads down doing the work. This website is where I explore what I'm learning along the way.
I run three AI brands: AIROI Association (B2C), Simple Academy (B2B), and SteveCunningham.ai (personal).
What I'm Obsessed With
I'm irrationally obsessed with how AI is going to change the future of work. I track every capability crossing viability thresholds. I map how those capabilities cascade through industries, companies, roles, and individual careers.
The predictions I made in 2023 are becoming reality now. The things I'm seeing today will be obvious by 2027.
The big picture. Where this is going over the next 1-3 years.
How that vision impacts how companies will operate.
The skills that create unfireable positions inside those companies.
How consultants will serve those champions and companies.
"The predictions I made in 2023 are becoming reality now. The things I'm seeing today will be obvious by 2027."Steve Cunningham
How to Engage
Coaching
Three times per month, one hour each. Ask me anything about what you're building, where you're stuck, or what you're seeing in your own work.
Small group sessions with peers operating at the same level. You get my real-time thinking on the problems you're actually facing, before those insights make it into books, events, or public content.
This is where the work happens. Active application with direct guidance.
Four intimate events per year. Curated cohorts. Venues designed for deep work. My latest thinking across all four focus areas.
Who Attends
Building or scaling in an AI-transformed market
Consultants, coaches, and agencies adapting delivery
Positioning for the Human+Agent economy
Monday, March 9, 2026
The Entrepreneurs Sandbox
Limited to 20 participants
Start your year with the latest synthesis amidst the Pacific. One full day of deep work in an environment designed for transformation.
Cooper's Row
Limited to 8 participants per session
Two intimate sessions in the heart of Texas. Small cohorts, deep work, and direct access to my latest thinking on building in the Human+Agent economy.
Wednesday, December 3, 2026
Victory Park
Limited to 20 participants
Close out the year with the final synthesis. One full day of deep work, reviewing what arrived and previewing what's next for the Human+Agent economy.
Lifetime Access
Stream from anywhere
All four events, every year
Lifetime access to recordings from all four events each year. My latest thinking, continuously updated as predictions arrive and new ones emerge.
Full-day live training with Steve, hands-on implementation sessions, small-group mastermind work, event workbook and resources, coffee and light breakfast, networking opportunities, and group dinner.
Airfare, hotel, transportation, meals outside provided coffee/pastries, recordings or post-event access (available separately), ticket transfers or refunds.
FAQs
All registrations are non-refundable and non-transferable. Cancellations after the registration deadline incur a $250 cancellation fee.
No. Each registration is for one attendee only and cannot be transferred.
No. These events are fully in-person and designed for hands-on learning. Digital recordings are available separately for those who cannot attend.
Oʻahu is confirmed at the Entrepreneurs Sandbox. San Antonio sessions are at Cooper's Row. Dallas is at Victory Park.
Please email Marisa Cunningham at marisa@simpleacademy.ai.
Four books mapping the cascade from economy to consultant. Each completely rewritten once per year as predictions arrive.
How to sell and deliver AI transformation services when credentials lag capability.
Read FreeThe context engineering methodology that took AI from 4% to 70.9% performance.
Organizational architecture for the transformation. The Information Factory model.
Where the market is moving. Which capabilities are crossing viability thresholds.
Effective Date: September 1, 2025
Company: 333 AI LLC
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Effective Date: September 1, 2025
Company: 333 AI LLC
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Effective Date: September 1, 2025
Company: 333 AI LLC
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