Winning With AI Makes a Stop in Milwaukee
Summer books solid and then February empties the calendar, and either way the writing piles up in the corner. That pile is what this Milwaukee evening works through, live on a screen, at a pace the whole room can follow. Pre-register and you hear the date before the announcement goes out.
Coming soon to Milwaukee, 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 Milwaukee

What is the seminar in Milwaukee, WI?
Winning With AI is a live, in person seminar coming to Milwaukee, and it is for owners, managers, and staff at small businesses of every type across the Milwaukee area. No industry is the audience, because the topic is the written work every business has to get through: answering customer questions, following up so a lead does not go cold, turning notes into quotes, proposals, or estimates, producing marketing in batches, reducing the scheduling back and forth, and handling routine written admin, which means summaries, checklists, instructions, and standard documents. The evening is also direct about what should stay away from these tools, that being pricing judgment, difficult customer conversations, and anything reputational. Mike Filsaime, 25 years into building companies including Groove, Kartra, WebinarJam, and EverWebinar, teaches it himself. Early bird seats are $49 while they last, and the registration fee is refunded if you attend and say before leaving the room that it was not right for you. No coding, no jargon, no prior experience, and nothing to buy when it ends. A Milwaukee date has not been announced, so pre-registration is the step open now.
- One Milwaukee evening, in person, and there is no recording to catch later.
- Any small business in the Milwaukee area belongs here, city side or out past the county line.
- $49 early bird while seats last, with the fee refunded if it was not right.
- Plain words the entire evening, and nothing to install before you come.
- Nothing is for sale afterward. No course, no membership, no renewal.
- No Milwaukee date is public yet. Pre-register and it comes to you first.
What does the evening in Milwaukee actually cover?
Nothing here is delivered off a slide. Each step happens live on a screen in a Milwaukee room, slow enough that people can write it down.
The subject is whatever writing already fills your week. A customer question that comes in after close. A quote request from last Monday that went cold. Notes off a job that need to become an estimate. Four weeks of posts and emails still not written. A scheduling exchange with no end. The same set of instructions retyped for the next new hire.
The evening spends real time on the other side too. Pricing stays a judgment call. So does the call with someone who is upset. So does anything published with your name on it. Drafting is the job these tools do, and drafting is where they stop.
Is AI worth it for a small business in Milwaukee, Wisconsin?
Early bird seats are $49 while they last. Come to the evening, and if it was not right for you, say so before leaving the room and the fee is refunded.
Willingness is not in short supply around here. Open hours are. A run from Bay View out to Brookfield and back takes a chunk of the afternoon. Lake effect snow takes a Tuesday. Festival season books the summer solid, and then it all has to be caught up in writing at ten at night.
The evening picks up that written load and puts it somewhere useful, while the human parts stay human. Steps written down, nothing following you home.
Why is this AI seminar built for Milwaukee businesses?
Nobody gets grouped by trade at this evening. A storefront in Walker's Point, a crew driving out to Oak Creek, an office in the Third Ward, all the same night.
A tuckpointing crew working Riverwest duplexes. A supper spot on Brady Street. A barbershop on North Avenue. A landscaping and plow outfit covering Wauwatosa and West Allis. A two person tax office on Mitchell Street. A gym in Bay View. A cleaning company running the north side. A dental office in Greenfield. A nonprofit in Walker's Point. An agent listing homes in Shorewood. A brake shop off Layton. Somebody packing online orders in a Cudahy basement. The written work is identical across all of them.
So the rule for stage time is simple. A step that only helps one kind of business does not appear.
What do Milwaukee attendees walk away with?
- Answer while the question is fresh. Someone writes after close and decides the next morning. Answers written ahead of time get yours there first.
- Follow up that keeps going without you. A lead who heard nothing back is not a lead who said no. Build the sequence once and let it run.
- Job notes into an estimate that reads clearly. What you wrote on the job becomes an estimate a customer can follow, in your wording, without an evening spent building it.
- Write the whole month in one sitting. The posts and emails that keep sliding get drafted together, then trimmed until they sound like your shop.
- One message settles the time. Picking a time by text runs five messages and still lands wrong. A plain way to close it in one gets covered.
- Standard paperwork done once. Checklists, summaries, instructions, the document you rebuild every month. Written once, pulled off the shelf after.
- Keep these away from the tools. Pricing, upset customers, anything public under your name. The line gets drawn clearly and the reason given.
Who is the Milwaukee seminar for?
What owners across the Milwaukee area get out of the Milwaukee evening
One storefront or several, the material is the same.
- Get the keyboard out of your evenings
- Serve more customers without adding people
- Leave with the first step chosen
What managers and shop leads get out of the Milwaukee evening
You already see where the hours vanish.
- End the tasks nobody should repeat
- Same result, a fraction of the typing
- Take back steps the crew can run
What solo owners and two person shops get out of the Milwaukee evening
The paperwork lands on you and stays there.
- Get replies out while you work
- Follow up without depending on memory
- Shut the laptop before midnight
How does a live seminar compare with free videos and an online course?
| This live seminar | Free online videos | Self-paced AI course | |
|---|---|---|---|
| Format | One Milwaukee evening, in the room with other owners | By yourself at a screen after hours | Weeks of modules on your own time |
| Fit | Every kind of small business in the Milwaukee area | Whatever a feed pushed at you | Written for a nationwide list |
| Questions | Asked aloud and answered before you go | Typed into a comment section | Sent off to a help desk |
| The steps | Done from start to finish in front of the room | Trimmed away to keep it short | Filmed in an older version of the tools |
| After it ends | Nothing to buy and nothing to renew | Nothing, and no next step | A monthly charge |
What is Milwaukee, WI actually like?
Milwaukee runs along Lake Michigan with the Menomonee Valley splitting it and I-94 carrying everything east and west. Downtown and the Third Ward move on foot, while Wauwatosa, West Allis, Oak Creek, and Brookfield move on drive time.
What everyone shares is a year split in two. Summer fills up fast and the work stacks up quicker than the paperwork can follow. Then one morning of lake effect snow in winter cancels the day's work. Driving from one end of Milwaukee County to the other twice in a day eats a real part of the day. Anything you can finish in writing from a phone in a parking lot saves you a second trip here.
That is the thinking behind the evening. Nothing shown asks for more than the computer already sitting on your desk.
How Milwaukee businesses are using AI right now
This is not a preview of what might come. Businesses across the Milwaukee area run pieces of it already, most of them without a single technical person on staff.
A four person tuckpointing crew quit writing estimates at night, because the measurements get dictated at the curb and come back written up in the owner's own words, read once and sent. A shop on Kinnickinnic that posted whenever somebody had a minute now drafts a month of emails and posts in one sitting. A small office that rewrote the same client instructions every week finally wrote them properly one time. A repair place in West Allis keeps written answers to its most common questions ready before the phone rings again.
Same outcome every time. The typing disappeared and the judgment stayed exactly where it was. Prices, hard conversations, and anything public remain the owner's call.
Who teaches the Milwaukee seminar?
Mike Filsaime put 25 years into building companies, and Groove, Kartra, WebinarJam, and EverWebinar came out of that time. Each one is software small businesses use to keep an ordinary day moving.
He speaks plainly. No acronyms, no assumed vocabulary. Instead of describing a tool, he opens it and does the job on screen, wording included, at a pace the room can keep.
In Milwaukee he works from the sort of backlog an owner in this area actually has sitting there, and does it live rather than talking about how it would go.
What do people who have seen this say about it?
When I saw what Winning With AI could do, I knew we had to move fast. Work that used to drag out for three months now gets delivered by my team in two or three days.
I'm a tougher critic, but Winning With AI blew me away. One idea showed me how to save thousands of dollars a month.
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.
When is the seminar coming to Milwaukee?
We have not set the Milwaukee 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 Milwaukee
What do people in Milwaukee ask about the seminar?
When will the Milwaukee seminar take place?
No date is set. Pre-registration is open here, and that list gets the Milwaukee date and venue before the public does, with the early bird price held while seats last.
Where in Milwaukee is the evening being held?
The room has not been picked. It will be in the metro with parking and a fair drive from most of the county, and pre-registered people learn the address first.
Is the Milwaukee seminar built for certain industries?
No. Contractors, shops, restaurants, salons, gyms, repair crews, landscapers, cleaners, real estate agents, accountants, law offices, dental and medical offices, nonprofits, online sellers, agencies, and one person operations are all who it is written for. The paperwork is common ground.
What does a Milwaukee seat cost?
Early bird seats are $49 while they last. Attend, and if it is not right for you, say so before you leave the room and your registration fee is refunded.
Do I need any background to attend in Milwaukee?
None. Nothing on the screen is code and nobody uses jargon. If you have used email and a phone you are ready.
What gets covered on the night in Milwaukee?
Customer questions, follow up before a lead cools, notes into quotes and estimates, marketing in batches, less back and forth over scheduling, and routine written admin. There is also a straight section on what not to hand over: pricing, difficult conversations, and anything reputational.
Who is teaching the Milwaukee evening?
Mike Filsaime. Groove, Kartra, WebinarJam, and EverWebinar came out of his 25 years of company building, and he runs every example live in the room.
Does the Milwaukee evening end with an offer?
No. No course, no subscription, and nothing to enroll in. The steps go home with you.
Is it worth bringing staff to Milwaukee?
Yes, if you can. Whoever answers messages and writes quotes will be running this daily, so they should hear it directly.
Where does the Milwaukee evening sit in the wider program?
The Milwaukee room is one stop on the Winning With AI seminar, 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