Winning With AI, an Evening in Chicago
Six or seven jobs eat the week in every small business in this city. Answering people. Chasing people who went quiet. Writing the quote. Writing the post. Settling on a time. Typing the same document again. For one evening in a Chicago room, those jobs get worked through in front of you, step by step. Pre-register and you hear the date and the venue before it is public.
Coming soon to Chicago, IL. The date and venue are not set yet. Pre-register to be the first alerted when they are.
Pre-register for the seminar in Chicago
What is the seminar in Chicago, IL?
Winning With AI is a live, in person seminar coming to Chicago, open to owners and teams from any small business in the city and across Chicagoland, whether that is a taqueria in Little Village, a plumbing crew out of Bridgeport, or a solo bookkeeper in Rogers Park. In one evening Mike Filsaime works through answering customer questions, following up so leads do not go cold, turning notes into quotes and proposals, producing marketing in batches, shrinking the scheduling back and forth, and handling routine written admin. Early bird seats are $49 while they last, backed by a money back guarantee. There is no coding, no jargon, no prior experience required, and nothing to buy afterward. A Chicago date has not been announced, so pre-registration is open.
- One evening, in person, in Chicago. Nothing recorded to catch up on later.
- Any small business in the city or the suburbs is welcome, no matter the trade or the storefront.
- Early bird seats run $49 while they last, with a money back guarantee.
- Plain language start to finish. No coding, no jargon, nothing you need to know first.
- Nothing to buy afterward. No course, no subscription, no software with a monthly bill.
- No Chicago date yet. Pre-register and you get told before anyone else.
What does the evening in Chicago actually cover?
One evening in a Chicago room, with the actual steps typed out where the room can see them. Not a talk about what AI might do by next year. The moves, in order, in front of people who run businesses in this city.
What gets covered is the work every business already has. The question a customer asks before deciding. The follow up on day three that nobody remembered to send. A stack of rough notes turned into a quote or an estimate. A month of marketing written on one afternoon. Five messages about a time reduced to one. The weekly summaries, the checklists, the instructions for somebody new, the standard document that gets rebuilt from scratch again.
You also get the shorter list, the one most people skip. Pricing calls stay with you. So does the conversation with an angry customer. So does anything that goes out publicly under your name. AI writes a draft, a person makes the call.
Is AI worth it for a small business in Chicago, Illinois?
A seat is $49 early bird while they last. Sit through it, and if it is not right for you, say so before you leave the room and your registration fee comes back. That is the arrangement, start to finish.
Effort is not what runs short in Chicago. Hours are. The message that sat unread until Tuesday. The estimate written at eleven at night. The month with no marketing because there was no time. Four emails to book one visit. The same form filled by hand for the twelfth time.
The evening is about moving that specific pile to something that is good at it, and keeping what needs a person. You take the steps home written down, and nobody asks you for anything after.
Why is this AI seminar built for Chicago businesses?
The room is open to anybody running a business in Chicago or the suburbs around it. Nobody checks what line of work you are in at the door.
A tuckpointing crew working the North Side. A restaurant in Pilsen. A salon on Devon Avenue. A landscaping company in Beverly. A two person accounting office in the Loop. A gym in Logan Square. A repair shop on Western. A cleaning company covering Oak Park and Cicero. A nonprofit in Humboldt Park. A real estate agent working Andersonville listings. An online seller packing boxes in Avondale. A dental office in Lincoln Square. Somebody who is the entire payroll. Behind all of it, the same paperwork.
Which is why every example on stage has to travel. If a step only works in one kind of business, it does not earn a slot.
What do Chicago attendees walk away with?
- Answer while they are still choosing. Inquiries in this city go out to more than one business at a time. Having quick, accurate answers ready for the questions you hear constantly means yours is the reply on the screen when they decide.
- Follow up that runs without you. The lead from last week is usually just unattended. You will see the follow up set up once so it keeps sending during a packed week, a dead week, and a week you spend out on jobs.
- Notes turned into a quote on the spot. Voice notes from the truck or a page of handwriting become a written estimate, proposal, or quote in your wording. The part that used to happen after dinner happens before you pull out of the alley.
- Stop facing a blank page every Monday. One idea turns into several weeks of emails, posts, and offers. The Monday job changes from writing something new to approving a batch and scheduling it.
- Take the negotiation out of scheduling. Settling on a time is the most avoidable back and forth in small business. There is a simple way to get it down to one message, and it gets built on stage.
- The dull written admin. Summaries, checklists, instructions for somebody new, the standard document you keep rebuilding. Least interesting stretch of the night, and usually the most heavily copied down.
- What never leaves your hands. Pricing judgment. The call with somebody who is upset. Anything public with your name on it. The evening is specific about where that line sits and why it does not move.
Who is the Chicago seminar for?
What owners of any business in Chicago or the suburbs get out of the Chicago evening
Storefront, van, office, kitchen. It changes nothing about the material.
- Move the writing and the chasing off your plate
- Handle more inquiries without another hire
- Walk out with steps you can set up this week
What managers and the people doing the work get out of the Chicago evening
You know exactly which hours of the week go to waste.
- Take the repetitive typing out of your crew's day
- Produce what gets asked for in a fraction of the writing time
- Be the one in the building who understands this
What one person shops and side businesses get out of the Chicago evening
You are the sales team, the office, and the labor.
- Reply like a company with staff behind it
- Keep every lead followed up with no assistant
- Stop giving your nights to paperwork
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 Chicago room, one evening, people around you who run businesses too | Your phone, by yourself, at midnight | A dashboard you quit opening after week two |
| Who it is for | Any small business in Chicago or Chicagoland, no trade requirement | Whoever the algorithm serves | A general audience and a general example |
| Getting your question answered | Ask it in the room, get the answer that night | A comment with no reply | A forum post that sits there |
| Watching it get built | Every step visible from start to finish | Edited down to the highlight | Filmed before the tools changed |
| What it costs you later | Nothing. No course, no subscription | Nothing, and no order to it either | Usually a recurring charge |
What is Chicago, IL actually like?
Chicago is a grid full of separate markets. Business on Archer Avenue does not look like business on Clark Street, and neither looks like the towers off LaSalle. Some blocks live on walk in traffic. Others never see the customer at all.
Two things hold across the whole map. People want an answer the same day, and a Friday afternoon call that goes to voicemail often gets made to somebody else on Saturday. And distance costs real time here. A drive from the South Side to a northwest suburb in February can take two hours round trip, so whatever can be settled in writing had better be settled in writing.
The evening is shaped around both. Nothing shown takes more than an afternoon to put in place.
How Chicago businesses are using AI right now
A lot of this is already happening around the city in small ways, with nobody technical involved.
A tire shop answers the five questions people ask before they bother calling. A caterer in Ukrainian Village turns a phone call into a written quote before the next one comes in. A studio in Wicker Park writes a month of posts in one Sunday sitting. A one person bookkeeping office turns a page of meeting notes into a clean summary and a task list. A snow removal outfit stopped playing email tennis over appointment windows. A hardware store on Milwaukee Avenue wrote its standard customer instructions once instead of retyping them per order.
No developer was involved in any of it, and no judgment changed hands. The pricing, the hard phone call, the public apology: still a person who knows the customer.
Who teaches the Chicago seminar?
The seminar in Chicago is headlined by Mike Filsaime, a pioneer in the AI and online business world and the founder of Groove, Kartra, WebinarJam, and EverWebinar. Hundreds of thousands of businesses around the world use his platforms to run their operations, host their events, manage their teams, and sell their products every day.
He is known for one thing above all: taking tools and technology that look complicated on the surface and breaking them down into the moves any business owner can actually execute without a computer science degree. No jargon. No theory. No watered-down explanation. Just the steps that work.
In Chicago, Mike brings that same approach to AI and walks local business owners and teams through the exact moves they can put to work immediately, with time for real questions and a focus on examples you can take home and use in your business the next morning.
What do people who have seen this say about it?
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.
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.
When is the seminar coming to Chicago?
We have not set the Chicago 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 Chicago
What do people in Chicago ask about the seminar?
Has a Chicago date been announced yet?
Not yet. Pre-registration is open here, and pre-registered people hear the Chicago date and venue before it is announced publicly, with the early bird price held while seats last.
What part of Chicago will the seminar be in?
The venue is not locked. It will be somewhere reachable by the L or a short drive from the suburbs, and the address goes to pre-registered attendees first.
Can any Chicago business owner attend, or is it aimed at one industry?
Any owner. A restaurant, a trades crew, a salon, a gym, a cleaning company, a law office, an accountant, a nonprofit, an online seller, a real estate agent, a shop, a one person operation. The evening deals with the paperwork every business has, so nothing in it depends on your industry.
What does a Chicago 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.
I am not technical. Will I keep up in Chicago?
Yes. It is plain language throughout, with no coding and no jargon. If you use email and a phone, nothing in the evening will be over your head.
What will the Chicago evening actually cover?
Answering the questions customers ask, following up so a lead does not drift to somebody else, turning notes into quotes and proposals and estimates, producing marketing in batches, cutting the back and forth out of scheduling, and routine written admin such as summaries, checklists, and standard documents. It also covers what to keep away from AI: pricing judgment, difficult customer conversations, and anything tied to your reputation.
Who is running the Chicago seminar?
Mike Filsaime. Twenty five years of building companies sits behind it, Groove, Kartra, WebinarJam, and EverWebinar among them, and he keeps the whole evening at the level of somebody who has never touched software for a living.
Is there a subscription after the Chicago event?
No. It is one evening. You leave with the steps, and there is nothing to enroll in and nothing billing you every month.
Can I send two people from my Chicago team?
Yes. The staff doing the repetitive work often get the most from it. Seats are individual, so register each person while early bird pricing lasts.
Where does the Chicago evening sit in the wider program?
The Chicago 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. Same teacher, same demonstrations, same money-back guarantee in every city; the examples change to match the businesses in the room.
Which other Illinois cities have a seminar page?
All Illinois cities | Every seminar city by state | AI for small business | Is an AI seminar worth it? | Who teaches it | Find a seminar near you