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 $995$495 · Remote $250

Save $500 — register by August 31, 2026

Three tracks, switch any time:Leadership TrackSales & Marketing TrackBuilder Track

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 · 10:3010:45
Break · 2:303 PM
8:30 – 9:00 AM · Everyone togetherWelcome: The Day AI Gets RealRod12:00 – 12:50 PM · Everyone togetherWorking Lunch: Watch a Business Dashboard Build ItselfTim & Greg3:00 – 4:00 PMLive AI Teardown: Bring Your Worst WorkflowTim4:00 – 4:30 PM · Everyone togetherYour 90-Day Roadmap: Leave With the PlanRod9:00 – 10:00 AMChatGPT, Claude, or Grok: A Straight-Answers Buyer's GuideRod & Rene10:00 – 10:30 AMHire Your First AI Employee (No Developers, No IT Department)Greg10:50 AM – 12:00 PMThe Owner's Cockpit: Every Number That Matters, One ScreenRene1:00 – 1:45 PMMore Bids. Better Margins. Construction Takeoffs With AI.Aaron1:45 – 2:30 PMWin More of the Right Work: Research Faster and Build Better Bids With AIAaron3:00 – 4:00 PMWhat Are We Doing About AI? Leave With the Answer.Rod & Rene9:00 – 9:45 AMGet Found by ChatGPT: SEO Is Now GEOAaron9:45 – 10:30 AMProposal Makeover: Rewrites That Win the JobAaron10:50 – 11:30 AMProfessional Video From an Image: Turn a Photo Into a Full Video With Your VoiceGreg11:30 AM – 12:00 PMA Month of Social Posts From One Job SiteGreg3:00 – 3:30 PMDirect Mail That Reads Minds: AI-Personalized PostcardsAaron3:30 – 4:00 PMThe One-Person Marketing Department: Your Q4 PlanAaron1:00 – 2:30 PMNever Let Another Lead Go Cold: The Follow-Up System That Runs ItselfJer9:00 – 10:30 AMClaude Code Bootcamp: Real Data to Live Dashboard by LunchTim10:50 AM – 12:00 PMWire AI Into Everything: Your Data, Your Apps, LiveTim1:00 – 2:20 PMOld ERP, New Tricks: Let AI Upgrade Your Line-of-Business SoftwareTim
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.

Every session names its instructor — tap through for their background and what you build in the room. Session materials are still being finalized and times 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.

Ready to join us in Spooner?

Tuesday, Sept 15, 2026 · The Island, Spooner WI · In person $995$495 · Remote $250 · Limited seats.

Save $500 — register by August 31, 2026