Winning With AI Comes North to Vermont
Most businesses in this state are small on purpose, so simple is the requirement and not a compromise. Burlington, Montpelier, Rutland, Brattleboro, St. Johnsbury, and the villages where the store, the garage, and the cafe sit on one block.
What is the seminar in Vermont?
Winning With AI is a single evening, in person, for Vermont business owners of every type, and it is built around small operations. You learn uses of AI that keep working after you set them up: answering customer questions, following up on leads, writing quotes from notes, producing marketing in batches, trimming the scheduling back and forth, and drafting routine written admin. No coding, nothing to maintain, and $49 early-bird while seats are open.
- Vermont has no city over 50,000 people, and Montpelier is the smallest state capital in the country.
- I-89, I-91, and Route 100 carry most of the traffic, and plenty of businesses live on the difference between them.
- Leaf season and ski season pack a large share of the year's customers into a handful of weeks.
- Village centers such as Woodstock, Manchester, and Stowe run on businesses with a few employees or none at all.
Which cities in Vermont have a seminar page?
- Burlington, VT · Coming soon. Pre-register to hear first.
- Montpelier, VT · Coming soon. Pre-register to hear first.
What happens on the night in Vermont?
A one person business has nowhere to put more work, which is why the evening sticks to six tasks and does them properly. Answering the questions customers ask again and again. Following up so a lead does not go cold while you are up on a ladder. Turning notes into a quote or an estimate. Writing marketing in batches. Cutting scheduling messages down. Drafting routine written admin such as summaries, checklists, instructions, and standard documents.
Nothing gets built that needs a person to keep it alive. That matters more in a small operation than anywhere else, because whatever breaks lands right back on the owner. Mike Filsaime, 25 years of building companies including Groove, Kartra, WebinarJam, and EverWebinar, teaches it in plain English and works every example live at the front of the room, so you watch the typing and the result rather than read a slide about them.
The room mixes the way a Vermont main street does: a plow and landscaping outfit, an inn, a bakery, a bookkeeper, a chiropractor's front desk, a nonprofit, a general contractor, a couple of people selling online, and several businesses that amount to one person and a phone. There is no course afterward and no subscription.
How business actually works in Vermont
Vermont does not have a metro, and that shapes every business in it. Burlington with its ring of Winooski, South Burlington, and Essex holds the largest cluster of people in the state, and the total is still under 150,000. From there the map is towns: Montpelier and Barre in the middle, Rutland out west, Brattleboro at the southern gate off I-91, St. Johnsbury and Newport up in the Northeast Kingdom.
The seasons run the calendar. Leaf season fills Route 100 and every inn along it for a few weeks in October. Winter fills Stowe, Killington, Sugarbush, and Mad River. Mud season empties all of it. A business here often earns a lopsided share of its year inside two short windows, then spends the quiet months on repairs, planning, and the paperwork that piled up.
Distance works differently than it does in a wide open state. Nothing is far in miles, but the roads are two lanes, they wind, and in February they are slow. Customers still expect an answer the same day. Owners here tend to know their customers by name, which is a real advantage, and to be the only person who can pick up the phone, which is the constraint this evening is about.
How Vermont businesses use AI right now
The repeat questions go first. An inn near Waitsfield gets asked about check-in times, dogs, and whether the road is plowed, over and over. AI answers in the innkeeper's wording and flags anything odd for a person. A bakery in Middlebury turns a list of what came out of the oven into a week of posts in one go. A firewood and plowing operation writes its route reminders once and sends them all winter.
Then the writing nobody charges for. A remodeler in Brattleboro dictates notes from a walkthrough and gets back an estimate laid out the way they always lay it out. A bookkeeper in Montpelier turns a client meeting into a summary and a task list. A village nonprofit drafts the standard sections of its annual letter, then a person rewrites the parts that need a human voice.
Follow-up and scheduling take the rest. The second message to the customer who asked in April goes out in May because the tool remembers and the owner does not have to. Appointments get set in two messages instead of seven. What never gets handed over is said plainly in the room: what to charge, the conversation with a customer who is unhappy, and anything published under the business name, which a person reads before it goes anywhere.
What do Vermont attendees take home?
- Simple enough that nothing needs maintaining. Everything shown gets set up once and then left alone. In a business where the owner is also the repair department, anything that needs babysitting gets abandoned by March, so none of it is built that way.
- The estimate written from a walkthrough recording. Talk through the job on the way back to the truck. AI turns that into the estimate in your usual layout, with your line items and your wording. You read it, fix what is wrong, and it goes out the same day.
- Repeat questions answered in your voice, not a robot's. You write the answers to the handful of things people always ask, once, the way you would actually say them. From then on those get handled, and anything unfamiliar comes straight to you.
- One sitting covers a stretch of marketing. Rather than scraping together a post between customers, you produce the batch at once: the emails, the posts, the seasonal announcement. Then you cut whatever reads like it came from somebody else.
- Two messages to book instead of seven. The tool offers open times, confirms the one they pick, and sends the reminder the day before. Over a week of appointments that is a lot of typing you never do again.
- The parts that stay yours, no exceptions. What you charge. The customer who is unhappy and wants to talk about it. Anything with your name on it going out in public. The evening names those directly so you are not guessing where the line sits.
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.
What do people in Vermont ask about the seminar?
Is the Vermont seminar useful if I am the only person in my business?
That is who most of the room is. When there is nobody to hand work to, the six tasks covered are the ones sitting on your own plate, and the whole evening is aimed at getting them off it without adding anything you then have to maintain.
When will Winning With AI hold an evening in Burlington or Montpelier?
Vermont dates are not scheduled yet. Pre-register and you get told first when a night lands near you, in Burlington, Montpelier, Rutland, Brattleboro, or elsewhere in the state, and pre-registering holds the $49 early-bird price while it is available.
Is the Vermont seminar built for one kind of business or all of them?
All of them. Contractors, shops, restaurants, inns, salons, gyms, repair crews, landscapers, cleaners, real estate agents, accountants, law offices, dental and medical offices, nonprofits, online sellers, and agencies all sit in the same room, because the work being handed to AI is identical across them.
What does a Vermont seat cost, and what if the evening is not for me?
$49 early-bird while seats remain. Attend, and if it is not right for you, say so before you leave the room and the registration fee is refunded. There is nothing sold at the end of the night.
Do I need any software before the Vermont seminar?
No. Nothing gets bought in advance and nothing gets installed. The tools shown run in a browser, and the free versions are enough to follow along. Bring a laptop or a phone and one real task out of your own week.
Where do the Vermont dates sit in the wider program?
Every Vermont room is one stop on Winning With AI live seminars, 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.