For CEOs & Owners · Sept 14–15 · Spooner, WI
Walk Into Your Next Board Meeting With the AI Answer
One day for the owner or CEO of an operations-heavy company: an honest read on where you stand with AI, straight answers on security and liability, and a written 90-day plan credible enough to take to the board.
Sound Familiar?
You own or run a 20–200 person operations-heavy company — a manufacturer, contractor, clinic, or field-services firm. You keep hearing AI is transformational, but you have nothing concrete to point to, and you'd rather not be the leader who missed it.
The Problem
You can't answer "what are we doing about AI?" with anything real — and you quietly worry about the other side of it: data security, client confidentiality, and what liability the company steps into the day AI touches real work.
What You Walk Away With
A scored AI maturity level, a written 90-day roadmap, and a plain-English read on AI security and liability.
Which One Are You?
The Next-Generation Successor
Inherited systems, inherited habits — and a market that stopped waiting.
Grandpa built it. Dad grew it. You get to be the one who future-proofed it — with a plan that fits the shop floor, not Silicon Valley.
The Owner / Founder
Every hour you stay the smartest system in the building, the business can't grow past you.
You built this company without asking permission — AI is no different. While competitors wait, you leave with an honest score of where you stand and the 90-day plan to turn it into distance.
The Hired CEO / Executive Director
The board asks "what are we doing about AI?" every quarter, and the honest answer is still "exploring."
One day turns "exploring" into a scored maturity level and a 90-day plan with your name on it — an answer, not an apology.
Your Sessions on the Leadership Track
Click any session for the full detail — what gets built, what you keep, and how it fits your day. Tracks run in parallel and you can switch at any time.
ChatGPT, Claude, or Grok: A Straight-Answers Buyer's Guide
The model landscape without the hype — what ChatGPT, Claude, and Grok each do best, what they cost, where your data actually goes, and the liability questions to settle before AI touches client work.
Session details
Hire Your First AI Employee (No Developers, No IT Department)
Stand up a working, tool-connected AI assistant for one real job in your business — reporting, follow-up, or scheduling. You describe the job in plain English; AI does the building.
Session details
The Owner's Cockpit: Every Number That Matters, One Screen
Turn the weekly questions you already ask into a live operational dashboard built from QuickBooks, your job system, and the spreadsheets in between.
Session detailsMore Bids. Better Margins. Construction Takeoffs With AI.
Bid more work without gambling your margin. Put a real plan set on screen and watch AI turn the current sheets and addenda into reviewable counts, lengths, areas, and assemblies — with every quantity linked back to its source. Your estimator verifies scale, units, gaps, and low-confidence items before anything moves into pricing.
Session detailsWin More of the Right Work: Research Faster and Build Better Bids With AI
More bids are not the goal — more profitable wins are. Start with a checked takeoff, then use AI to research the project, owner, general contractor, requirements, deadlines, and risks; make a disciplined go/no-go decision; apply your company's real costs; and assemble a bid your team can defend.
Session detailsWhat Are We Doing About AI? Leave With the Answer.
Turn the day's demos into an operating plan your company can actually run. See the same workflow side by side as a reusable prompt with human review and as a tool-connected agent with triggers, approvals, and measurement — then design the first lift for your own business.
Session detailsPlus the Sessions Everyone Shares
The day opens and closes together — and ends with every attendee holding a written 90-day roadmap.
Welcome: The Day AI Gets Real
Session detailsWorking Lunch: Watch a Business Dashboard Build Itself
Session detailsLive AI Teardown: Bring Your Worst Workflow
Session detailsYour 90-Day Roadmap: Leave With the Plan
Session detailsBring Both Sides of the House
The retreat works best when leadership and the hands-on team hear it the same day. Here's what it looks like from the other seats:
Hands-On AI Training Within Driving Distance
The retreat draws ceos & ownersfrom across western Wisconsin and Minnesota — most within a few hours by car of The Island in Spooner, WI. Can't travel? Attend every session live remote, or explore all our AI training for business options.
For CEOs & Owners — Frequently Asked Questions
Ready to spend the day with us?
Tuesday, Sept 15, 2026 · The Island, Spooner WI · In person $495 (working lunch included) · Remote $250 · Limited seats.