Madison, Winning With AI Takes the Typing
By nine at night the doors are locked and the writing starts. That is the pattern for most owners on the isthmus and everywhere around it, and it is exactly what one live evening in Madison takes apart on screen. The overdue proposal, the follow up nobody sent, the month of marketing at zero. Pre-register and the Madison date arrives before the advertising does.
Coming soon to Madison, WI. The date and venue are not set yet. Pre-register to be the first alerted when they are.
Pre-register for the seminar in Madison
What is the seminar in Madison, WI?
Winning With AI is one live evening, in person, coming to Madison, and it is built for owners of small businesses of every kind across the area, with no industry favored and none excluded. What it covers is the written work every business carries: answering the questions customers send in, following up before somebody drifts off, turning job notes into a quote, proposal, or estimate, writing marketing in batches, trimming the back and forth that booking a time takes, and the standing admin of summaries, checklists, instructions, and standard documents. The same evening is clear about what to keep these tools away from, which is pricing judgment, the conversation with a customer who is already upset, and anything reputational that carries your name in public. Mike Filsaime teaches it after 25 years of building companies, Groove, Kartra, WebinarJam, and EverWebinar among them. Early bird seats are $49 while they last, and if you attend and decide before leaving the room that it was not right for you, the registration fee is refunded. There is no coding, no jargon, no experience required, and no course or subscription afterward. Madison does not have a confirmed date yet, so pre-registration is what this page does.
- One evening in Madison, in person, and nothing gets recorded.
- Small businesses of every kind around Dane County are welcome.
- $49 early bird while seats last, refunded if it is not for you.
- Ordinary language start to finish, with nothing to set up first.
- No course after, no subscription, and no pitch at the end.
- Madison's date is not set. Pre-registered names hear it first.
What does the evening in Madison actually cover?
The night runs on one screen and a lot of questions. Mike builds each step in front of the room slowly enough that people can write it down as it happens.
Everything demonstrated comes from ordinary business days. An inquiry that showed up at eleven on a Sunday. Notes from a walkthrough near Monroe Street waiting to become a written quote. Four weeks of unwritten marketing. A set of shift instructions being retyped for the second time this year.
The last stretch is about limits, and it is the part people repeat afterward. Pricing is a call you make, and it stays with you. So does the reply to an angry review. So does anything going out in public with your name attached.
Is AI worth it for a small business in Madison, Wisconsin?
The early bird seat costs $49 while they last. Attend, and if it is not the right evening for you, say so before you leave the room and the registration fee is refunded.
Time, not work, is the thing in short supply. A stop in Verona and a stop in Sun Prairie look manageable until the Beltline stacks up at four, and the rest of the afternoon belongs to traffic.
So the writing slides to nine at night. What the evening does is hand that block of the week back, without moving a single decision out of your hands.
Why is this AI seminar built for Madison businesses?
The room is a mix on purpose. Two owners who sell nothing alike end up comparing notes at the break, because the paperwork on both of their desks turned out to be the same paperwork.
A remodeling crew working the near west side. A supper club out past Middleton. A barbershop on Willy Street. A landscaping outfit covering Verona and Fitchburg. A bookkeeper near Hilldale. A gym off East Washington. A cleaning company running McFarland and Monona. A dental office on Odana Road. A nonprofit near Capitol Square. An agent listing on the east side. A repair shop on Park Street. Somebody packing online orders in a Schenk-Atwood basement. Same written work in all of them.
That is the filter for the agenda. If a step only helps one kind of business, it does not get stage time.
What do Madison attendees walk away with?
- The reply that lands first. Most people hire whoever gets back to them soonest. Written answers, ready in advance, go out without you drafting anything.
- Follow up without reminders. A customer going quiet is not a decision. The follow up gets built during the evening and keeps sending after you leave.
- Notes into a quote. The measurements from a walkthrough come back as something a customer can read, worded like you, typed by nobody at ten at night.
- Marketing in batches. A month of emails and posts drafted in one sitting, then cut back until it reads like your business instead of a template.
- Booking with less back and forth. Setting a time should not take a whole thread. That exchange gets rebuilt on screen while the room watches it shrink.
- Write the document once. Checklists, instructions, summaries, the report due every month. Built properly a single time and reused after.
- What never gets handed over. Pricing, angry customers, and anything the public will read with your name on it. The evening is direct about that line.
Who is the Madison seminar for?
What madison owners behind a counter or a wheel get out of the Madison evening
One evening fits both.
- Take the writing off your night
- Do more work at current headcount
- Leave with one step decided
What the person stuck with the admin get out of the Madison evening
You know exactly what repeats.
- Quit rewriting standard documents
- Same output, far less typing
- Bring back a process anyone can run
What one person shops and small crews get out of the Madison evening
There is nobody to hand it to.
- Reply while you are still working
- Keep follow up moving
- Finish earlier at night
How does a live seminar compare with free videos and an online course?
| This live seminar | Free online videos | Self-paced AI course | |
|---|---|---|---|
| Setting | A Madison room full of local owners | A laptop at the kitchen table | Weeks of solo modules |
| Audience | Small businesses of every kind near Madison | Whoever the feed chose | Written for everyone and no one |
| Questions | Answered out loud, on the spot | Dropped in a comment thread | Emailed and waited on |
| The demonstration | Built live from an empty screen | Cut short to keep viewers | Filmed before the last update |
| After it ends | Nothing sold and nothing recurring | The next video autoplays | A monthly charge continues |
What is Madison, WI actually like?
Madison is squeezed onto an isthmus between Mendota and Monona, with the Beltline sweeping the south side, John Nolen running in along the water, and East Washington pointing at the Capitol from the other direction.
Geography funnels everything here. There are only so many ways across, so a five mile trip is either quick or it is not, depending entirely on the hour. Business gets found by word of mouth on a block or a corridor more than by advertising. Winter shortens the day and pushes the desk work well past dark.
That is the frame around the evening. Nothing shown on screen assumes a budget past what is already on your desk.
How Madison businesses are using AI right now
Plenty of Madison businesses already run parts of this without calling it anything. No consultant, no technical hire, just an owner who set it up on a slow afternoon.
A flooring crew on the west side quit typing quotes after supper, because the numbers get spoken into a phone in the driveway and come back written the way the owner talks. A cafe on Willy Street that posted whenever someone remembered now blocks one morning a month for the whole batch. A two person bookkeeping office near Hilldale wrote its client onboarding instructions once and stopped rewriting them every January. A ski and bike shop off the Capital City Trail keeps written answers ready for the questions that repeat every season.
Nobody handed over a decision. What they handed over was typing. The price, the hard conversation, and anything that ends up public stayed exactly where it was.
Who teaches the Madison seminar?
Madison's evening is taught by Mike Filsaime, whose 25 years of building companies produced Groove, Kartra, WebinarJam, and EverWebinar.
The reason people follow him is that he refuses to talk over anybody. Terms get explained in ordinary words, no background is assumed, and a step gets performed on screen rather than described from a slide.
What that looks like in Madison is a room where somebody names the task they keep avoiding, and it gets built in front of them before the night ends.
What do people who have seen this say about it?
I had no coding experience. No technical background. Nothing. After seeing how to use AI in plain English, I built software and workflows that completely changed my company.
My project lead was wearing too many hats, and the team felt it. This one event showed us how AI could take that work off people's plates. The impact on our sanity has been massive.
Thank you for your incredible knowledge and insight. It made a powerful impact. I don't take anyone's time lightly, least of all someone with your level of marketing genius.
He'll not only make it simple, he'll make it very profitable.
When is the seminar coming to Madison?
We have not set the Madison date yet. Pre-register and you will be the first to know when we do, before seats go on sale to everyone else.
Pre-register for the seminar in Madison
What do people in Madison ask about the seminar?
When is Winning With AI coming to Madison?
The date is open at the moment. Pre-registering here is how the Madison date and venue reach you before the ads go out, with the early bird price held while seats remain.
Where in Madison will the seminar take place?
The venue is not settled. It needs to be reachable without crossing the isthmus at rush hour and it needs parking that does not ruin the night, and pre-registered people get the address first.
Is the Madison evening built for a specific industry?
No. Shops, contractors, restaurants, salons, gyms, cleaners, repair crews, landscapers, accountants, law offices, real estate agents, dental and medical offices, agencies, nonprofits, online sellers, and one person operations are all the right audience. Their paperwork overlaps almost completely.
What does a Madison seat cost?
$49 early bird while seats last. If you attend and it turns out not to be right for you, say so before you leave the room and the registration fee is refunded.
Do I need a technical background for the Madison seminar?
No. No code appears and no term goes unexplained. If you can use email on a phone, you have what is needed.
What will the Madison evening cover?
Customer questions, follow up before someone goes cold, notes turned into quotes and estimates, marketing produced in batches, scheduling with less back and forth, and the routine written admin. One section is entirely about what to keep away from these tools: pricing, difficult conversations, and anything reputational.
Who teaches the Madison seminar?
Mike Filsaime. He spent 25 years building companies, including Groove, Kartra, WebinarJam, and EverWebinar, and in Madison every example is typed live in front of the room.
Can I bring my staff to the Madison evening?
Yes, and most owners who do say it worked better that way. Two people who watched the same build tend to finish the setup instead of talking about it.
Is anything sold after the Madison seminar?
No. No course, no subscription, nothing pitched from the stage. The notes you take are what you go home with.
Where does the Madison evening sit in the wider program?
The Madison room is one stop on the Winning With AI program, the touring live AI seminar Mike Filsaime teaches one evening at a time in cities across the United States. Same teacher, same demonstrations, same money-back guarantee in every city; the examples change to match the businesses in the room.
Which other Wisconsin cities have a seminar page?
All Wisconsin cities | Every seminar city by state | AI for small business | Is an AI seminar worth it? | Who teaches it | Find a seminar near you