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AI Business Retreat 2026

The Full Agenda

Two days at The Island in Spooner, Wisconsin. One evening to settle in, one full working day across three tracks — and nobody leaves with homework. You leave with it done.

Sept 14–15, 2026The Island · Spooner, WIIn person $495 · Remote $250
Three tracks, switch any time:Leadership TrackSales & Marketing TrackBuilder Track
For CEOs & Owners →For Senior Leaders →For Employees & Builders →

Monday, September 14

The Night Before

Social · Optional4:30 – 8:00 PMFire pit · BYOB

Prompt & Pour

Roll in the evening before and start the easy way — an unstructured cocktail evening by the fire pit. No agenda, just instructors and attendees trading prompts and ideas.

Tuesday, September 15

The Working Day

Morning and closing sessions bring everyone together; the rest of the day splits into three parallel tracks — laid out below like stages at a festival, so you can see exactly what runs at the same time. Click any session for the full details, what you'll build, and who it's for.

Swipe sideways to compare all three tracks

Leadership Track

CEOs & owners

Sales & Marketing Track

Senior leaders

Builder Track

Hands-on builders

8:30
9 AM
9:30
10 AM
10:30
11 AM
11:30
12 PM
12:30
1 PM
1:30
2 PM
2:30
3 PM
3:30
4 PM
4:30
Break · 10:30 – 10:45
Break · 2:30 – 2:55
8:30 – 9:00 AM · Everyone togetherWelcome: The Day AI Gets Real12:00 – 12:50 PM · Everyone togetherWorking Lunch: Watch a Business Dashboard Build Itself2:55 – 3:55 PMLive AI Teardown: Bring Your Worst Workflow3:55 – 4:30 PM · Everyone togetherYour 90-Day Roadmap: Leave With the Plan9:00 – 10:00 AMChatGPT, Claude, or Grok: A Straight-Answers Buyer's Guide10:00 – 10:30 AMHire Your First AI Employee (No Developers, No IT Department)10:50 AM – 12:00 PMThe Owner's Cockpit: Every Number That Matters, One Screen1:00 – 1:45 PMMore Bids. Better Margins. Construction Takeoffs With AI.1:45 – 2:30 PMWin More of the Right Work: Research Faster and Build Better Bids With AI2:55 – 3:55 PMWhat Are We Doing About AI? Leave With the Answer.9:00 – 9:45 AMGet Found by ChatGPT: SEO Is Now GEO9:45 – 10:30 AMProposal Makeover: Rewrites That Win the Job10:50 – 11:30 AMProfessional Video From an Image: Turn a Photo Into a Full Video With Your Voice11:30 AM – 12:00 PMA Month of Social Posts From One Job Site1:00 – 1:45 PMDirect Mail That Reads Minds: AI-Personalized Postcards1:45 – 2:20 PMThe One-Person Marketing Department: Your Q4 Plan2:55 – 3:55 PMNever Let Another Lead Go Cold: The Follow-Up System That Runs Itself9:00 – 10:30 AMClaude Code Bootcamp: Real Data to Live Dashboard by Lunch10:50 AM – 12:00 PMWire AI Into Everything: Your Data, Your Apps, Live1:00 – 2:20 PMOld ERP, New Tricks: Let AI Upgrade Your Line-of-Business Software
4:30 – 7:30 PM· Optional evening social — hors d'oeuvres on the lake

All times Central. Tap any session for full details — one registration covers every track, and you can switch tracks at any time.

Session times and materials are still being finalized — the agenda may be refined between now and September, but the shape of the day (three tracks, hands-on sessions, and a written 90-day roadmap to close) is locked.

See the Day Through Your Eyes

The retreat looks different depending on the seat you sit in. Pick the page written for yours.

For CEOs & Owners

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.

Your day, mapped out

For Senior Leaders

You Were Told to "Make AI Happen." Leave With It Happening.

One day for the GM, ops leader, sales leader, or office manager who actually owns the workflow: a repeatable method, proof on data like yours, and one real workflow that runs itself before you're back at your desk.

Your day, mapped out

For Employees & Builders

Stop Playing With AI. Start Shipping With It.

One day for the hands-on builder: wire AI to real data, build a tool-connected agent with guardrails, and go back to work with something running — plus the language to make the case internally.

Your day, mapped out

Ready to join us in Spooner?

Tuesday, Sept 15, 2026 · The Island, Spooner WI · In person $495 · Remote $250 · Limited seats.