AI Business Retreat 2026
A full-day, hands-on AI retreat for business leaders at The Island lakeside lodge in Spooner, WI — attend in person ($495 per person, working lunch included) or remote ($250 per person), hosted live by AIBMM Certified Coaches. Come the night before for Prompt & Pour, build all day across two tracks, then unwind at the evening social. Leave with your maturity level scored, a prompt playbook, a working agent, a scoped RapidDashboard.AI pilot, and a 90-day roadmap.
Rod Holum
Certified AIBMM Coach & Speaker — Coulee Tech
Everything You Need to Know
The night before, the venue, the day itself, your speakers, 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 $495 · Remote $250 · Limited in-person seats. Tell us who you are and we'll hold your spot.
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 afternoon tracks
- 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 afternoon splits into a business track and a developer track, so bring both sides of the house and leave with a shared plan.
In the Room — or Remote, Hosted by a Certified Coach
In Person — The Island, Spooner WI
$495 per person
The full experience: work side-by-side with all three 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, 5:00 to 8:00 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.
The Day at a Glance
Morning together, afternoon in tracks, roadmap before you leave. Every block ends with an artifact you keep. Full timed agenda below.
Discover: Score Your Maturity
All Together • Levels 1–2Rod and Aaron open the day with a live AIBMM assessment of every organization in the room. We cover the foundations nobody skips — AI usage policy, data guardrails, and surfacing the hidden AI use already happening inside your walls. By the first break, you know your level.
The Level 2 Masterclass: Prompts That Run the Business
Aaron Libner • Level 2Most of the room lives here, so we master it. Aaron — a sales and non-profit pro — builds prompt playbooks live for the work that actually moves your numbers: pipeline follow-up, donor and grant communications, proposals, board reporting. Template-driven, human-reviewed, ready for your team Monday.
The Bridge: Working Lunch + RapidDashboard.AI Live Demo
Live Demo • Level 2 → 3Over lunch, we show what the other side of the bridge looks like: live business data answering plain-English questions. Prompt-to-dashboard. Prompt-to-report. This is the moment the room shifts from we use ChatGPT sometimes to our data reports to us.
RapidDashboard.AI
Your business data. One question away.
Afternoon Tracks: Build at Levels 3 & 4
Choose Your Track • Levels 3–4The room splits. Track A — Business Transformation with Rod and Aaron: build agents and scope your operational cockpit, no code required. Track B — the Developer Track with Tim: engineer production agent systems with real architecture and real code. Both tracks ship something before they end.
Plan & Advance: Your 90-Day Roadmap
All Together • Take It HomeThe AIBMM cycle is Discover, Plan, Advance — and we close by writing the plan. Every attendee (in-person and remote, guided by their coach host) leaves with a written 90-day roadmap: the specific milestones and criteria to reach their next maturity level.
Choose Your Build
Both afternoon tracks build working systems at Levels 3 and 4 — the difference is who is doing the building.
Track A — Business Transformation
For owners, executives, sales leaders, non-profit directors, and operations managers. Build agents and stand up your operational cockpit — no code required. Led by Rod Holum with Aaron Libner.
Track B — The Developer Track
For developers, technical leads, and IT directors. Engineer production-grade agent systems — real architecture, real code, real deployment discipline. Led by Tim Holum.
Bringing a team? Send leadership to Track A and your builders to Track B. You reconvene for the roadmap session and leave with a plan both sides already agree on.
The Schedule — Tuesday, September 15
All times Central. Remote cohorts run the same agenda live with their coach host.
Morning — Everyone Together
| Time | Session | You leave with |
|---|---|---|
| 8:00 | Doors open, coffee & registration — remote cohorts run their tech check with their coach host | — |
| 8:30 | Welcome: Operational Transformation in One Day — Rod Holum | The map for the day |
| 8:45 | Discover: Live AIBMM Assessment + Governance Foundations — Rod & Aaron | Your scored maturity level |
| 9:45 | Break | — |
| 10:00 | The Level 2 Masterclass: Prompts That Run the Business — Aaron Libner | Your prompt playbook |
| 11:15 | Working Lunch + The Bridge: RapidDashboard.AI Live Demo (lunch included in person) | Your weekly-questions shortlist |
| 12:15 | Track split — pick your room | — |
Afternoon — Choose Your Track
| Time | Track A — Business Transformation | Track B — Developer |
|---|---|---|
| 12:30 | Build Your First Agent (Rod) | Anatomy of a Production Agent (Tim) |
| 1:00 | Sales & Mission Workflows That Run Themselves (Aaron) | Multi-Agent Systems That Ship (Tim) |
| 1:30 | Break | Break |
| 1:45 | Stand Up Your Operational Cockpit (Rod) | Extend the Cockpit — Hands-On (Tim) |
| 2:15 | Manage AI Like a Team (Rod) | Ship It: Prototype to Production (Tim) |
Closing — Everyone Together
| Time | Session | You leave with |
|---|---|---|
| 2:45 | Plan & Advance: Write Your 90-Day Roadmap — all instructors + remote coach hosts | Your written 90-day roadmap |
| 3:20 | Close: Your Next Level | Next steps & follow-up schedule |
| 3:30 | Done for the day | — |
Evening — Optional Social
| Time | What |
|---|---|
| 5:00 – 8:00 | Hors d'oeuvres & hanging out with the faculty and fellow attendees — for everyone in the area or staying overnight. The best conversations of the day happen here. |
Business Transformation with Rod Holum & Aaron Libner
The journey from using AI to managing AI — built around your actual operations, not demos.
Build Your First Agent
Rod • Level 3The jump from chatting with AI to AI that does the work. Rod builds a tool-connected, repeatable agent workflow live — researching, drafting, and executing a multi-step business task with full traceability — then walks you through doing the same for a workflow you brought with you.
Sales & Mission Workflows That Run Themselves
Aaron • Level 3 AppliedAaron takes the morning's playbooks and connects them: pipeline follow-up that drafts itself from your CRM, donor stewardship sequences, grant pipelines, and board reports that assemble their own numbers — with human review gates exactly where they belong.
Stand Up Your Operational Cockpit
Rod • Level 3 → 4Working session on RapidDashboard.AI: pick the system you would connect first (ERP, accounting, CRM), define the questions leadership asks every week, and scope the governance — row-level security, audit trails, who sees what. You leave with a pilot scoped and shovel-ready.
RapidDashboard.AI
The platform Track A scopes a pilot on
Manage AI Like a Team
Rod • Level 4The Level 4 shift: multiple agents working together under governance and QA. What to measure, where the human checkpoints go, and how the org chart changes when your people stop doing the work and start managing the systems that do.
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
Both tracks put hands on it: Track A scopes a pilot for your KPIs, and Track B extends the platform with custom connectors and tools. This is what shovel-ready means — you can start the pilot the week after the retreat.
The Developer Track with Tim Holum
Engineering agentic systems that survive contact with production — high Level 3 into Level 4, taught from working code.
Anatomy of a Production Agent
Tim • Level 3+Inside a real recursive agent loop: analyze, decide, act, learn. Tool registries, structured outputs, cost budgets, exit conditions, and the anti-fabrication guardrails that keep agents honest — patterns pulled from systems running in production today, not slideware.
Multi-Agent Systems That Ship
Tim • Level 4When one agent becomes a team: orchestration patterns, shared state, QA gates between agents, observability, and cost control. How to decide what gets its own agent, what stays a tool, and where the human approval boundaries belong.
Extend the Cockpit
Tim • Level 3 → 4Hands-on with RapidDashboard.AI from the builder's side: custom data connectors, new tools, and governed automations on top of the platform. The goal is to ship a working extension against sample data before the track ends.
RapidDashboard.AI
The platform Track B builds on
Ship It: Prototype to Production
Tim • Level 4 OperationsThe unglamorous part that makes it real: deployment gates, idempotent migrations, integrity checks, monitoring agents in production, and the runbook for when an agent goes sideways. Operational transformation means it runs every day — not just on demo day.
Three Instructors, Three Vantage Points
Aaron Libner
Sales & Non-Profit Pro • Levels 2–3
Aaron translates AI into revenue and mission outcomes. He leads the morning Level 2 masterclass and the applied sales and non-profit sessions in Track A — prompts and workflows for people whose job is people.
Rod Holum
Certified AIBMM Coach • Levels 3–4
Rod leads the transformation arc of the day — from first agent to managed AI systems. He hosts the monthly AIBMM webinar and coaches businesses through the maturity model across Wisconsin, Florida, and beyond.
Tim Holum
Lead Developer • Levels 3–4
Tim builds the production agentic systems the other tracks talk about — multi-agent platforms, tool registries, and governed automations. He teaches the Developer Track from working code.
Remote cohorts are facilitated live by AIBMM Certified Coaches, so every attendee — in the room or on the screen — works through the day with expert guidance.
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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