Jer Holum
AI Coach & Systems Builder
AI Coach, Coulee Tech · Founder, Web Devy · La Crosse, WI
Jer Holum was programming robots in elementary school, founded and ran a La Crosse web design company called Web Devy while his classmates were looking for summer jobs, and used AI heavily in every part of his life, school and work alike, all the way through high school. He is the youngest coach on this faculty and the only one who never had to be converted: there is no earlier way of working for him to unlearn.
Save $500 — register by August 31, 2026
What Jer's Work Actually Produces
Every other coach in the building learned to work one way and then rebuilt around AI. Jer never had a before. That is not a charming detail, it is the entire argument of the day standing in the room: this is what one person can build when the tools were never new to them and nobody told them to wait their turn. If you have been wondering whether to hand your youngest employees real leverage and real authority, he is the answer to that question, and you can ask him about it directly.
Web Devy
a web design company he founded and ran
His own business in La Crosse, building websites for local businesses, started while most people his age were applying for a first job.
2024
co-author, Buttkicking IT Support
Written with Rod Holum and published in September 2024: the Coulee Tech story and what "buttkicking" IT support actually looks like.
90 min
the longest working build on the sales track, and it is his
Never Let Another Lead Go Cold is the afternoon's long block, where the morning's search, proposal, video, and mail work gets wired into one measurable revenue loop. You leave with a blueprint, not notes.
The Long Version
Robots first, prompts much later
He was writing programs for robots in elementary school, sequencing a machine to carry out instructions before most kids have written a five-paragraph essay. The order matters more than the novelty does. He learned that a system does exactly what you told it and nothing you meant, at an age when that lesson is just how the world works rather than a hard-won professional correction. Everything he builds now still starts from that assumption.
He started a company instead of waiting for one to hire him
Web Devy was his own web design business in La Crosse, building sites for local businesses, and it was one of several ventures he started and ran rather than waited around for. Small, and unusual: real clients, real deadlines, and someone else's money on the line, at an age where most résumés list a sports season. Having run it means he has already had the conversation where a customer describes what they want, means something else, and needs the finished thing on Tuesday. That is a different education from any course.
AI was never a new tool he had to fit in
He used AI heavily in every part of his life, school and work both, all the way through high school. That sentence reads as unremarkable until you set it against the rest of the faculty, who all describe adopting AI: a decision, a transition, a set of habits deliberately changed. Jer has no adoption story because there was nothing to adopt from. He did not learn these tools as a professional skill, he learned them the way you learn a language you grew up speaking, which is why he is fluent in the parts most people never get to. When he needs something built, using AI to build it is not a strategy he selected, it is the shape the work has always had. That is why his sessions skip the persuasion and go straight to construction.
Friday nights and Sunday mornings
He played football for the Holmen Vikings, under a coach who turns up in Wisconsin's AI Leadership Blueprint for 2024, the book Rod co-authored with Aaron Libner. That is a smaller world than it sounds like, and it is the point: in this valley the people building with AI and the people coaching Friday nights are frequently the same people. He also runs sound and video at First Free Church in Onalaska, which is live production for a full room, where there is no undo, no second take, and no explaining afterwards that it usually works. That is a real engineering apprenticeship dressed up as a volunteer shift. Systems that have to survive live, in front of people, with a hard start time, are built differently from systems that only have to demo well, and the difference shows up in what he ships.
He co-wrote the company's book
Buttkicking IT Support, the Coulee Tech story and the philosophy underneath it, carries the byline "Rod & Jer Holum" and was published in September 2024. It is the one piece of his work a stranger can go buy and read for themselves.
What he builds now
Jer coaches owners on putting AI to work in the field, and he builds the systems that catch what a busy business drops. The one he teaches at the retreat is follow-up: the machinery that notices a new lead, does the research, drafts the right next touch, stops for a human to approve it, and writes the result back to the CRM. It is unglamorous, it is where most of the money leaks out of a small business, and it is exactly the kind of work that rewards someone who assumes it should have been automated in the first place.
Credentials
- Co-author, Buttkicking IT Support
- Published September 2024 with Rod Holum: the Coulee Tech story and the service philosophy behind it.
- Founder, Web Devy
- His own web design company in La Crosse, Wisconsin, which he founded and ran, building sites for local businesses. Client work, on client deadlines.
- Programming robots in elementary school
- He started with machines that do exactly what they are told, years before he started with software that pretends to understand you.
- AI-native since high school
- Not an adoption story, a default. He used these tools heavily in every part of his life, school and work alike, and has never built anything in a world without them.
- Live production: sound and video
- Runs audio and video at First Free Church in Onalaska. Live, weekly, in front of a full room, with no take two.
- Holmen Vikings football
- Played for the program at Holmen High School.
See Jer at the Retreat
- When
- Tuesday, Sept 15, 2026
- Day job
- Coulee Tech
- Speaks elsewhere
- Rarely. The retreat is his public date
- Where
- The Island · Spooner, WI (or attend live remote)
- Price
- In person
$995$495 · Remote $250
Save $500 — register by August 31, 2026
One registration covers the full retreat — every session, every track.
All 20 sessions
See the full retreat agenda →
What Jer Speaks On
Jer does not work a speaking circuit. He builds, and he coaches owners who are trying to build. These are the subjects he can take apart live, with the system open in front of you, and the failure modes still attached.
- Never Let a Lead Go Cold: The Follow-Up System That Runs Itself
- Speed to Lead: Instrumenting the One Sales Number That Moves First
- Templates vs Agents: The Same Follow-Up at Two Maturity Levels
- The Human Gate: Where Approval Belongs in an Automated Loop
- AI-Native: How Somebody Who Started With It Actually Works
- After the Click: What a Small Business Website Should Do Next
- Empowering Your Youngest Employees: What Happens When You Get Out of the Way
- Live Production Discipline: Building Things That Cannot Fail in Front of a Room
At the retreat
Jer teaches the Sales & Marketing Track's longest working block, Never Let Another Lead Go Cold, from 1:00 to 2:30, where the day's separate marketing pieces get wired into one follow-up engine you can measure. He is also the person to find in the hallway if the question on your mind is really about people rather than software: what a 20-year-old with these tools and actual authority can build for your company, and how much of your bench you have been quietly under-using. One registration covers all three tracks, so you can drop into his room for one session and go back to yours.
Sessions Jer Teaches
Jer leads 1 sessionon September 15 and is on site for the whole day. One registration covers all 20 sessions across the Leadership, Sales & Marketing, and Builder tracks — so you are never locked out of a room.
Also Close to Jer's Work
Taught by other faculty, but squarely in Jer's lane — worth the hallway conversation afterward.
The One-Person Marketing Department: Your Q4 Plan
with Aaron Libner
Session details
Direct Mail That Reads Minds: AI-Personalized Postcards
with Aaron Libner
Session detailsHire Your First AI Employee (No Developers, No IT Department)
with Greg Brainerd
Session details
Get Found by ChatGPT: SEO Is Now GEO
with Aaron Libner
Session detailsJer Holum — Questions & Answers
Spend a day in the room with Jer Holum.
Six instructors, three tracks, twenty hands-on sessions — and a written 90-day AI roadmap you leave with. Sept 15, 2026 · The Island, Spooner WI · or attend live online.
Save $500 — register by August 31, 2026