Illinois, Winning With AI Is On the Way
The state runs nearly 390 miles from the Wisconsin line down to Cairo, and a Rogers Park barber has the same pile of unanswered messages as a tire shop in Marion. Bring the laptop you actually work on, because the practice happens in the room.
What is the seminar in Illinois?
Winning With AI is one live evening in Illinois, taught in person, and it is built for owners of every kind of business. A Berwyn heating crew, a taqueria in Pilsen, a Champaign bookkeeper, a Rockford salon, a nonprofit in Peoria, and somebody shipping orders out of a Naperville garage all learn the same handful of moves: answering customer questions, keeping leads from going cold, turning notes into quotes and proposals, building marketing in one sitting, cutting the back-and-forth over scheduling, and clearing routine written admin. Mike Filsaime teaches it in plain English, with no code, no jargon, and no experience assumed, and there is no course or subscription waiting at the end. Early-bird seats are $49 while they last, and if you attend and it is not right for you, say so before you leave the room and the registration fee is refunded.
- Illinois stretches nearly 390 miles from the Wisconsin border down to Cairo, so Chicago and the southern tip sit closer to other states than to each other.
- Chicago is divided into seventy-seven community areas, and an owner on Devon Avenue works a different customer base than one six miles off in Bridgeport.
- Interstates 55, 57, 70, 74, 80, and 90 all cross the state, which is why so much of an Illinois workday happens behind a windshield.
- Outside the Chicago area the trade centers stand well apart: Rockford, Peoria, Springfield, Champaign-Urbana, the Quad Cities, and the Metro East towns across the river from St. Louis.
Which cities in Illinois have a seminar page?
- Chicago, IL · Coming soon. Pre-register to hear first.
- Springfield, IL · Coming soon. Pre-register to hear first.
What happens on the night in Illinois?
Treat it as one long working session rather than a talk. Nothing gets installed, nothing gets sold at the door, and every job is done on screen while you follow along on your own device. The chores that stack up in an Illinois week get finished in the room: the reply you have typed a hundred times, the estimate that waits until Sunday night, a month of posts and emails written in one pass.
Mike Filsaime teaches the evening. He has spent twenty-five years building companies, Groove, Kartra, WebinarJam, and EverWebinar among them, and he explains this the way one owner explains something to another. No jargon, nothing to install in advance, and every example worked live instead of described.
How business actually works in Illinois
Cook County is its own world. The Loop and West Loop live on office hours and lunch traffic, Lincoln Square and Andersonville run on neighborhood regulars, Pilsen and Little Village trade in Spanish half the day, and the towns along the Kennedy and the Eisenhower pull customers in three directions at once.
The ring roads changed who competes with whom. Naperville, Aurora, Schaumburg, and Joliet each grew into a full market of their own, and a crew based in one of them can cover the other three without ever driving into the city.
Downstate is main streets and long drives. Rockford and the Quad Cities look toward Wisconsin and Iowa, Peoria and Bloomington-Normal hold the middle, Springfield fills up when the legislature sits, Champaign-Urbana empties every summer, and the Belleville and Edwardsville side does its business on St. Louis time. Owners covering that ground write their paperwork after supper.
How Illinois businesses use AI right now
Customer questions answered without retyping. Do you deliver to Oak Park, what does it run, can you come Saturday. AI writes each reply in your own wording and keeps a list of who is still waiting on you.
Follow-up that does not depend on your memory. The caller who went quiet in March is ready in September, and the check-in gets drafted and sent while the name is still on the list.
Notes turned into a quote. Talk the job through into your phone in a driveway in Berwyn and get a clean estimate back on your own template, with your terms already sitting where they belong.
Marketing built in batches. One sitting produces a month of posts, a few emails, and the words for a flyer or a sandwich board, all about the work you actually do.
Less back-and-forth over times. Confirmations, reminders, and reschedules get written for you, along with the routine paperwork: summaries, checklists, instructions for a new hire, and the standard documents you keep rebuilding from scratch.
Part of the night covers what to keep away from it. Pricing takes judgment and stays with you. So does the customer who is already angry, and anything that could follow your name around afterward.
What do Illinois attendees take home?
- Done In Front Of You. The request goes up on the screen, the job gets finished while you watch, and then you run the same thing on your own business with help still standing there.
- Bring The Laptop You Use. Your own device, your own customers, your own half-finished paperwork. Practice on real work beats practice on an example built for a slide.
- Every Trade In One Room. Contractors, shops, restaurants, salons, gyms, repair crews, landscapers, cleaners, real estate agents, accountants, law offices, dental and medical offices, nonprofits, online sellers, agencies, and owners doing all of it alone. None of these tools ask what you sell.
- Where AI Does Not Belong. Pricing, the hard conversation with somebody already unhappy, and anything your reputation rides on belong to a person. The evening marks that line where you can see it.
- Nothing Sold At The Door. No course, no subscription, no upsell at the back of the room. Early-bird seats are $49 while they last, and if the evening is not right for you, say so before you leave and the registration fee is refunded.
What do people who have seen this say about it?
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 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.
What do people in Illinois ask about the seminar?
When is Winning With AI coming to Chicago or another Illinois city?
Illinois dates are being set now, with Chicago and the collar counties first in line and Springfield, Rockford, Peoria, and the Quad Cities behind them. Pre-register and you hear first when a date is confirmed, and the $49 early-bird price is held for your seat.
Is the Illinois evening aimed at one kind of business?
No. The room is mixed on purpose. Contractors, 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 sit through the same evening, because the chores eating their hours are the same chores.
I have never used AI. Can an Illinois owner follow along in a single night?
You can. Everything is typed in ordinary English, the way you would explain a task to somebody on their first shift. Mike works each example live, takes questions from the room, and there is nothing to set up beforehand.
What does an Illinois seat cost, and what happens if the night is not useful?
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 the registration fee is refunded.
What should an Illinois business keep away from AI?
Pricing decisions, the customer who is already upset, and anything reputational. Those belong to a person, and part of the evening is spent marking that boundary clearly.
Where do the Illinois dates sit in the wider program?
Every Illinois room is one stop on Winning With AI, the touring live AI seminar Mike Filsaime teaches one evening at a time in cities across the United States. The teacher, the demonstrations, and the money-back guarantee are the same in every city; the examples change to match the businesses sitting in the room.