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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.

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Tue, Sep 15, 2026
8:00 AM CDT
Spooner, WI
In person $995$495 · Remote $250 · Limited seats

Save $500 — register by August 31, 2026

The Full Agenda

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.

Monday, Sept 14

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

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.

Open the agenda page

Save $500 — register by August 31, 2026

Your Instructors

World-Class Coaches — In the Room With You

Six instructors who run real businesses and teach this for a living: four certified AIBMM coaches, the developer who builds the systems they teach, and the coach who runs the afternoon's long follow-up build. Small room, hands-on all day — you work beside them, not behind a webcam.

Rod Holum speaking on stage to a full room at an AI business conference
Rod Holum on the AIBMM keynote stage — the same material, taught hands-on at The Island.

Why it lands differently

  • They run the businesses too. An Inc. 5000 IT and cybersecurity firm, a 20-year Gulf Coast MSP, and a Houston MSP already running private AI on its own operations — the examples come from their own P&L, not a case-study deck.
  • Security is built in, not bolted on. Three of the six are career cybersecurity practitioners, so every AI workflow you build gets pressure-tested.
  • Six instructors, three tracks. Leadership, Sales & Marketing, and Builder run in parallel — so you are never sitting in a session written for someone else's job.
Rod Holum

Rod Holum

Certified AIBMM Master Coach

CEO & Founder, Coulee Tech

Holmen, WI

Rod is the CEO and founder of Coulee Tech — an Inc. 5000–recognized IT and cybersecurity firm — and an award-winning author and speaker helping leaders adopt AI responsibly and securely.

  • Inc. 5000 founder
  • Award-winning author
  • AI strategy & cybersecurity
Speaker Profile
Aaron Libner

Aaron Libner

Certified AIBMM Executive Coach

President, Coulee Tech — Eau Claire Market

Eau Claire, WI

Aaron helps business leaders simplify technology and use AI and cybersecurity to grow with confidence. Known for an engaging, “non-geek speak” style, he presents across the Midwest to owners, sales teams, and non-profit boards.

  • 20+ years B2B sales & leadership
  • Manufacturing, healthcare & professional services
  • President, Fierce Freedom
Speaker Profile
Rene Miller

Rene Miller

Certified AIBMM Executive Coach

CEO & Co-Founder, Ener Systems

Covington, LA

A mechanical engineer turned AI strategist, Rene helps CEOs and CFOs turn AI into a force multiplier — scaling teams, cutting costs, and driving competitive advantage without compromising security.

  • CISSP-certified
  • 20+ years running an MSP
  • Speaks nationally to CFO groups
Speaker Profile
Greg Brainerd

Greg Brainerd

Certified AIBMM Coach

Founder & CEO, Braintek

Houston, TX

Greg founded Braintek in 2002 and grew it into one of Houston's established managed IT providers. His team now builds private, local AI into real operations — ticket triage, an AI operator technicians talk to, and live dashboards out of QuickBooks and ERP data.

  • 20+ years running an MSP
  • Cybersecurity author
  • Private AI in production
Speaker Profile

Tim Holum

Builder Track Instructor

Software Developer & Co-Founder, Coulee Tech

La Crosse, WI

Tim brings 20 years of high-level development and engineering expertise. He builds the production agent systems the other tracks talk about — and teaches the Builder Track from working code, not slides.

  • 20 years software engineering
  • Agent architecture & platform builds
  • Co-founder, Coulee Tech
Speaker Profile

Jer Holum

AI Coach, Coulee Tech

AI Coach, Coulee Tech · Founder, Web Devy

La Crosse, WI

The youngest coach on the faculty and the only one with no adoption story. Jer was programming robots in elementary school, founded and ran the La Crosse web design company Web Devy, and used AI heavily in every part of his life, school and work alike, all the way through high school. He co-wrote Buttkicking IT Support with Rod and runs the afternoon's longest build: the follow-up system that makes sure no lead ever goes cold in an inbox.

  • Co-author, Buttkicking IT Support
  • Founder, Web Devy
  • AI-native since high school
Speaker Profile

Attending remotely? Live cohorts are hosted by AIBMM Certified Coaches running the same exercises with your group in real time — ask us about hosting one.

At a Glance

Everything You Need to Know

The night before, the venue, the day itself, where to stay, and how to get here — without scrolling.

Prompt & Pour
The Night Before

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

The Retreat

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.

The Framework

The 5 Levels of AI Business Maturity

Every session of the day is pinned to a level of the AI Business Maturity Model. You start the morning by scoring where you actually are, and you leave with a written plan for the next level — not a general enthusiasm for AI.

  1. 1

    Level 1

    AI Drifter

    Uncontrolled, unstructured AI exposure. Using AI sporadically with no strategy or guidelines.

    A few people paste company information into ChatGPT. Nobody owns it, nobody reviews it, and nobody knows what left the building.

    Curiosity, and real exposure you can't see.

  2. 2

    Level 2

    Prompted Operator

    You are probably here

    Template-driven prompting with human review. Using AI with standard templates and approved workflows.

    Saved prompts your team actually reuses, with a human checking the output before it ships. Faster writing, faster research — but AI still can't see your systems.

    Hours back every week. This is where most businesses are today.

  3. 3

    Level 3

    Agent Builder

    Where the retreat takes you

    Tool-connected, repeatable agent workflows. AI agents that execute defined steps with traceability.

    AI is connected to a real system — your CRM, your job data, your accounting — and runs a multi-step task end to end while you watch each step.

    A job that used to take a person a day now runs on request.

  4. 4

    Level 4

    Agent Manager

    Where the retreat takes you

    Multi-agent orchestration with governance and QA. Managing multiple AI agents that work together with oversight.

    Several agents handing work to each other on a schedule, with permissions, audit trails, and a QA step — managed the way you'd manage a team.

    Capacity that scales without adding headcount.

  5. 5

    Level 5

    Physical Integrator

    Embodied automation with real-world execution controls. AI integrated into physical processes and hardware.

    AI reaching past the screen — production lines, equipment, and physical processes with real-world execution controls.

    The frontier. Very few businesses are here yet.

Attend Your Way

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.

Featured Platform

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.

See RapidDashboard.AI

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.

Minneapolis, MNSt. Paul, MNEau Claire, WILa Crosse, WIHudson, WIDuluth, MNRochester, MNWausau, WIRice Lake, WISt. Cloud, MN

AI Business Retreat — Frequently Asked Questions

Start by figuring out where you actually are today, then follow a structured path instead of running random experiments. The AI Business Retreat does exactly that in one day: you complete a live AI maturity self-assessment, build a reusable prompt playbook for your real tasks, connect AI to an actual tool to create a working agent, and leave with a written 90-day roadmap to your next level.
The AI Business Maturity Model (AIBMM) is a five-level framework that maps a company's progression from scattered AI use to managed AI systems: (1) AI Drifter, (2) Prompted Operator, (3) Agent Builder, (4) Agent Manager, and (5) Physical Integrator. The retreat dedicates one hands-on session to each level, so you leave knowing exactly where you stand and what comes next.
Level 1 AI Drifter — sporadic, unstructured AI use. Level 2 Prompted Operator — template-driven prompting with human review. Level 3 Agent Builder — tool-connected, repeatable agent workflows. Level 4 Agent Manager — multiple AI agents orchestrated with governance. Level 5 Physical Integrator — AI embedded into physical processes. Most businesses today sit at Level 1 or 2.
The AI Business Retreat is a one-day, in-person AI training held at The Island in Spooner, Wisconsin — an easy drive from Minneapolis–St. Paul (about 2 hours), Eau Claire, Hudson, Duluth, and La Crosse. If you can't travel, you can attend live remotely for $250. It's built for business owners and leaders across western Wisconsin and Minnesota who want practical AI skills, not theory.
Yes. The Leadership and Sales & Marketing tracks are designed for owners, operators, and managers with no coding background — you'll tie AI to real ROI in plain English. There's also a parallel Builder track for technical staff who want to build production agent systems, so you can bring your whole team and split up.
Yes. Instead of only watching demos, you'll connect AI to an actual tool and build a repeatable agent workflow live — watching it research, draft, and execute a multi-step task with full traceability. You also leave with a prompt playbook, a scoped RapidDashboard.AI pilot, and a written 90-day roadmap.
In-person registration is $495 if booked by August 31, 2026 (then $995), and includes a working lunch and all hands-on sessions at The Island in Spooner, WI. Remote (live online) attendance is $250. Seats are limited. The optional Prompt & Pour social on the evening of Monday, September 14 is included for in-person attendees (BYOB).
Tuesday, September 15, 2026, 8:30 AM–4:30 PM Central, at The Island in Spooner, Wisconsin, with an optional Prompt & Pour kickoff the evening before. Most attendees fly into Minneapolis–St. Paul (MSP) and drive up, or use the regional Eau Claire (EAU) and Duluth (DLH) airports.
You don't pay. Under the AI Guarantee, Coulee Tech invoices after the retreat, not before, and if you don't feel the day exceeded your expectations, you tell us and the invoice is voided. No fine print and no gotcha clauses.

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