AI Business Retreat 2026
A full-day, hands-on AI retreat at The Island lakeside lodge in Spooner, WI — 20 working sessions across three tracks (Leadership, Sales & Marketing, and Builder), everything on real business data. In person $495 through Aug 31, 2026 (then $995) or remote $250. Come the night before for Prompt & Pour, and leave with your AI maturity scored, a working tool-connected agent, and a written 90-day roadmap.
Save $500 — register by August 31, 2026
20 Sessions. Three Tracks. One Written Plan.
This is a working day, not a conference. Three tracks run side by side — pick your column, switch any time, and click any session for the full detail of what you'll build there.
Prompt & Pour · 4:30 – 8:00 PM · Fire pit · BYOB — roll in the night before and trade prompts by the fire. Then the main event, Tuesday:
Swipe sideways to compare all three tracks
Leadership Track
CEOs & owners
Sales & Marketing Track
Senior leaders
Builder Track
Hands-on builders
All times Central. Tap any session for full details — one registration covers every track, and you can switch tracks at any time.
Save $500 — register by August 31, 2026
Built for the Seat You Sit In
A CEO, a sales leader, and a hands-on builder each get a different day. See 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 outFor 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 outFor 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 outEverything You Need to Know
The night before, the venue, the day itself, where to stay, and how to get here — without scrolling.
Prompt & Pour
Roll in the evening before and start the easy way — an unstructured cocktail evening by the fire. BYOB, no agenda, just instructors and attendees trading prompts and ideas.
- Monday, Sept 14 · 4:30 – 8:00 PM
- BYOB — bring your own beverage
- Fire pit at The Island, Spooner WI
Ready to join us in Spooner?
In person $995$495 · Remote $250· Limited in-person seats. Tell us who you are and we'll hold your spot.
Save $500 — register by August 31, 2026
Operational Transformation — Not Just Another AI Talk
Last year's retreat helped leaders turn AI into profit. This year goes further. Profit is a side effect — the real prize is operational transformation: changing how work actually flows through your business, with AI systems that carry real load.
The entire day is structured around the AI Business Maturity Model (AIBMM), and every session is built on one rule: nothing theoretical — only shovel-ready work. You will not leave with a notebook full of ideas. You will leave with work product:
- Your AIBMM maturity level, scored — a live assessment of where your organization actually stands
- A prompt playbook — working, reviewed templates for your team's highest-volume tasks
- A working tool-connected agent — built during the track sessions
- A scoped RapidDashboard.AI pilot — your KPIs, your systems, ready to connect
- A written 90-day roadmap — specific criteria for advancing to your next maturity level
Who should attend: Business owners, executives, sales and non-profit leaders, operations managers — and your developers. The day runs three parallel tracks — Leadership, Sales & Marketing, and Builder — so bring both sides of the house and leave with a shared plan.
In the Room — or Remote, Hosted by a Certified Coach
Register by August 31, 2026 and save $500 on an in-person seat.
In Person — The Island, Spooner WI
$995$495 per seat
Regularly $995 — book by August 31, 2026 to lock in $495
The full experience: work side-by-side with the instructors at a lakeside lodge, whiteboard your workflows over a working lunch (included), and write your 90-day roadmap with a coach at your table. Come in the night before for Prompt & Pour, and stick around after for the evening social, 4:30 to 7:30 PM.
Remote — Coach-Hosted Cohorts
$250 per person
Every session streams live. Remote cohorts are hosted by AIBMM Certified Coaches who run the same exercises with your group in real time — same agenda, same artifacts, from your own conference room.
Are you an AIBMM Certified Coach? You can host a remote cohort for your own clients — reach out and we will set you up.
The 5 Levels of AI Business Maturity
Most businesses arrive at Level 2 — using AI through prompts, with nothing connected to real systems. The AIBMM gives you a structured progression out of that plateau, and this retreat is engineered to move you toward Levels 3 and 4 — where AI is connected to your tools and managed like a team.
AI Drifter
Uncontrolled, unstructured AI exposure. Using AI sporadically with no strategy or guidelines.
Prompted Operator
Template-driven prompting with human review. Where most businesses are today — and where the retreat meets you.
Agent Builder
Tool-connected, repeatable agent workflows. AI agents that execute defined steps with traceability.
Agent Manager
Multi-agent orchestration with governance and QA. Humans managing AI systems that do real work.
Physical Integrator
Embodied automation with real-world execution controls. AI integrated into physical processes and hardware.
RapidDashboard.AI — The Level 3–4 Play
Most businesses are stuck at Level 2: AI answers whatever you type at it, but it is blind to your actual business. RapidDashboard.AI is the fastest bridge across — it connects securely to the systems you already run (ERP, accounting, CRM, healthcare platforms) and turns plain-English questions into live dashboards and narrative reports. Your business data. One question away.
- Level 3 in practice: tool-connected AI working against your real operational data — OEE by line, AR aging, utilization — instead of copy-pasted spreadsheets
- Level 4 in practice: governed reporting with row-level security, audit trails, and SSO — AI your compliance officer can sign off on
- Approved AIBMM delivery: implemented by AIBMM Certified Coaches, so the rollout follows the same maturity framework the retreat teaches
Every track puts hands on it: leadership scopes a pilot for your KPIs while builders extend the platform with custom connectors and tools. This is what shovel-ready means — you can start the pilot the week after the retreat.
The Island — Spooner, Wisconsin
We are getting out of the conference room. This year the retreat is held at The Island, a lakeside lodge in Spooner in Wisconsin's Northwoods — open water, fire pits, and northern quiet. The kind of place where you actually think clearly and the best conversations happen between sessions.
Lakeside Lodge
Room to spread out, whiteboard, and breathe — not a windowless ballroom.
Working Lunch Included
In-person seats include lunch on-site, so the day keeps its momentum.
Northwoods Setting
Spooner, WI — easy to reach, hard to leave. Make a trip of it.
Prompt & Pour — Monday, September 14
Roll in the evening before and start the retreat the easy way. Prompt & Pour is an unstructured cocktail evening by the fire — BYOB (bring your own beverage), no agenda, no slides. Just instructors and fellow attendees swapping prompts, war stories, and what they are hoping to build the next day.
When
Mon, Sept 14 • 4:30–8:00 PM
Where
The Island, Spooner WI
Bring
Your own beverage
Then the main event kicks off the next morning — doors at 8:00 AM, welcome at 8:30. Staying overnight nearby is the move; lodging is below.
Lodging — Rice Lake Is Your Home Base
Make a night (or two) of it. Rice Lake is about 20 minutes from the venue and has the most rooms and easiest options — start there. There is also a stay right in Spooner if you want to be next door to the lodge. Book early; September fills up in the Northwoods.
Rice Lake, WI — ~20 minutes away
Right in Spooner, WI — closest to the venue
Drive times are approximate. Booking links open a map search so you can compare rates and reserve directly.
Flying In
Spooner sits in northwest Wisconsin. Most out-of-town attendees fly into Minneapolis–St. Paul and make the easy drive up; two regional airports are closer if the schedule works.
MSP
Minneapolis–St. Paul
~2 hours by car • the main hub, most flights and rental cars
EAU
Eau Claire, WI
Regional • closer drive, limited schedule
DLH
Duluth / Superior, MN
Regional • northern approach
Driving? The venue is The Island in Spooner, WI. Get directions →
Discover. Plan. Advance.
The retreat follows the AIBMM three-step methodology:
- Discover — a guided self-assessment identifies your organization's current maturity level.
- Plan — you build a structured 90-day roadmap with specific criteria for advancing to the next level.
- Advance — you leave with the roadmap, the playbook, a working agent, and a scoped dashboard pilot — shovel-ready work, not ideas.
In person: $495 per person (working lunch included) · Remote: $250 per person, hosted live by an AIBMM Certified Coach. In-person seats are limited to keep the lodge hands-on, and remote cohort slots are scheduled with coach hosts in advance — reach out early.
Hands-on AI training within driving distance
Business owners travel to Spooner from across western Wisconsin and Minnesota — most within a few hours by car. Can't make the drive? A $250 live-remote seat is available.
AI Business Retreat — Frequently Asked Questions
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