Hawaii CEO Summit — Try It First

Experience the
Operating System

Not sure if this is for you? Come try it. One full day. Experience the complete system, meet the room, and see if this is where you belong. We cover our costs. You decide if you want more.

Date March 9, 2026
Time 9:00 AM — 5:00 PM
Location Entrepreneur's Sandbox — Honolulu, HI
After-Event Dinner to follow
Reserve Your Spot — $1,500
Steve Cunningham

The Most Valuable Day of Your Quarter

I overhaul my CEO AI operating system every week. New tools, new patterns, new ways to extract leverage. Once a quarter, I download everything I've learned to you — and we collaborate with some of the smartest, most dedicated CEOs on the planet.

This is an arbitrage opportunity. While other CEOs are drowning in AI noise — hype cycles, demos that don't translate — you're installing systems that actually run your business. This is how you out-compete every other CEO you compete against.

Every quarter, you leave operating at whatever level I've reached. The system compounds. You compound. The gap between you and your competition widens.

This peer group exists for CEOs who want to become elite of the elite. Not just AI-aware. Not just AI-curious. AI-dominant. Understanding every arbitrage opportunity before your competitors even know it exists.

This is that room.

01

Elite Guidance

The world's leading coaches and consultants in every functional area — proactively working for you 24/7.

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02

Relentless Execution

The world's largest army of executors ready to execute flawlessly. No waiting. No limitations.

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03

1000x Leverage

The compounding advantage you take with you for the rest of the quarter. That's the arbitrage.

10 Functional Areas. 10 Arbitrage Opportunities.

An expert strategist and relentless execution team for every functional area of your business. If you don't have one, you do now. If you already do, you bring this arbitrage back to them every quarter. See what nobody else sees. Execute before anyone else knows what's happening.

01

Strategy

See market shifts, competitive threats, and hidden opportunities months before your competitors. Synthesize signals they're not even tracking. Make moves while they're still reading last quarter's reports.

02

Products

Identify the features that will matter before customers know they want them. Ship faster than teams twice your size. Turn product development from a bottleneck into a weapon.

03

Marketing

Launch campaigns in hours, not weeks. Test messaging at a scale that would bankrupt competitors. Find the channels and angles nobody else has discovered yet.

04

Sales

Respond to opportunities instantly. Personalize at scale. Follow up relentlessly without burning out your team. Close deals while your competitors are still scheduling discovery calls.

05

Operations

Spot inefficiencies before they become problems. Document and optimize processes that used to run on tribal knowledge. Scale without the chaos that usually comes with it.

06

IT

Maintain systems that would normally require a dedicated team. Troubleshoot faster. Keep documentation current. Turn technology from a cost center into a force multiplier.

07

Finance

See the financial picture in real-time, not 30 days later. Forecast with precision. Catch anomalies instantly. Make decisions with clarity your competitors don't have.

08

HR-Admin

Hire faster. Onboard better. Keep policies current without dedicating headcount to it. Build the team you need without the administrative drag that slows everyone else down.

09

Legal

Review contracts in minutes, not days. Stay ahead of compliance. Protect the business without becoming paralyzed by risk. Move fast and don't break things.

10

Continuous Improvement

The system that improves all the other systems. Find bottlenecks before they hurt. Deploy upgrades constantly. This is how the gap between you and your competition keeps widening.

Schedule — March 9, 2026

Full-Day Event: 9:00 AM – 5:00 PM

9:00 AM

State of the System

What's changed since last quarter. New breakthroughs. New tools. New patterns that are working.

10:00 AM

Operating System Deep-Dive

Live walkthrough of my current setup across all 10 functional areas. Real files. Real workflows.

12:30 PM

Working Lunch

Peer exchange and Q&A

1:30 PM

Hands-On Implementation

Build your systems with direct support. Real work, real progress.

4:00 PM

90-Day Commitments

What you'll complete before next quarter. Accountability built in.

5:00 PM

Close & Dinner

Wrap-up followed by group dinner (location TBD)

What You Get

  • My complete, current operating system — files, processes, quality controls
  • Updates reflecting the latest AI capabilities and what's actually working
  • A full day of hands-on implementation with direct support
  • A curated room of high-performing CEOs implementing at the same level
  • The chance to see if this peer group is right for you

Location

Entrepreneur's Sandbox — Honolulu, Hawaii

This Pays for Itself

Every CEO is paying vendors to do work that can now be done in-house — faster, better, and at a fraction of the cost. Marketing agencies. Consultants. Contractors. Service providers charging premium rates for work that AI can do better.

As part of the full membership, we conduct a full AI Insourcing Audit of your vendor relationships. We identify exactly which functions you can bring in-house, how to do it, and what you'll save.

The savings from insourcing alone will pay for the membership. Usually multiple times over. This isn't an expense — it's an arbitrage opportunity with a clear ROI.

What We Audit

  • Marketing & creative services
  • Content production
  • Research & analysis
  • Administrative services
  • Legal document prep
  • Financial reporting
  • Customer support
  • Technical documentation
Typical Finding $100K–$500K+ in annual savings

Experience the Room

Not ready to commit to a full membership? Come try it. Experience the complete day, meet the CEOs in the room, and see if this is where you belong. We cover our costs — you decide if you want more.

Your Trial Includes

  • Full access to the quarterly session
  • My complete, current operating system
  • All files, processes, templates, and quality controls
  • Hands-on implementation support during the session
  • Access to the curated peer group for the day
  • No obligation — decide after you experience it
Try It — Hawaii
$25,000
$1,500
one-time trial
  • Full day experience
  • Complete operating system
  • Hands-on implementation
  • No commitment required

March 9, 2026 · Entrepreneur's Sandbox · Honolulu, HI · 9 AM–5 PM · Dinner to follow

Reserve Your Spot
Steve Cunningham

Steve Cunningham

I've trained over 10,000 professionals on AI methodology. Senior partners at the world's biggest executive search firms have called this work "magical." I'm a deep practitioner in what I call the humans + agents economy—the emerging model where people and AI work together to create leverage, not chaos.

I'm the author of Humans+Agents for Professional Services Firms, the first book in a four-part series exploring how organizations can build sustainable operating models with AI agents. The series continues with Humans+Agents Operator, Humans+Agents Company, and Humans+Agents Economy—each examining a different scale of transformation.

My work is grounded in real-world execution. I focus on ROI and measurable outcomes, helping entrepreneurs, consultants, and organizations move beyond AI experimentation into systems that actually run their businesses. The CEO OS you'll see at this event is the methodology I use every day.

This summit takes place in Hawaii at the Entrepreneur's Sandbox, a purpose-built venue designed for focused work and meaningful collaboration. Away from day-to-day distractions, the setting creates the conditions for immersive work, intentional connection, and clear next steps you can immediately apply in your business.

Frequently Asked Questions

It's the full experience at cost. You get the complete quarterly session — the operating system, the hands-on implementation, the peer group — for $1,500. We cover our costs. You decide if you want to continue with a full membership.

A curated peer group of high-performing CEOs. Four times a year, we spend a full day together where I transfer my exact operating system — the files, processes, and quality controls I use to run my entire business with agents across all 10 functional areas.

Not technical at all. This is designed for CEOs and business operators, not programmers. If you can use modern AI tools like ChatGPT or Claude, you have everything you need.

Any size. The operating system scales. Whether you're a solo operator or running a large organization, the methodology applies. The goal is the same: go from 1x to 10x to 100x to 1000x as a CEO.

My complete, current operating system — the actual files, processes, templates, and quality controls I use across all 10 functional areas. Updated every quarter with whatever I've learned and implemented since the last session. Plus hands-on implementation time and a curated peer group.

If you decide this is the room for you, you can apply for the annual membership ($50,000/year) which includes all four quarterly sessions plus the full AI Insourcing Audit. The trial is designed to let you experience it before committing.

Email marisa@simpleacademy.ai with any questions about the Hawaii summit or the trial experience.