Winning With AI Arrives in Massachusetts
One evening, in person, and the tools stay open on screen the whole time. Owners drive in from Boston, Worcester, Springfield, Lowell, and the Cape, bring a laptop, and run each step against their own business before they leave.
What is the seminar in Massachusetts?
Winning With AI is a single live evening, in person, open to Massachusetts business owners of every kind: trades, shops, restaurants, salons, gyms, repair crews, offices, nonprofits, agencies, online sellers, and one-person operations. Mike Filsaime works through AI on ordinary business tasks in plain language: answering customers, following up on leads, drafting quotes and proposals, producing marketing, sorting out scheduling, and handling routine written admin. No coding, no jargon, no prior experience, and no course to buy afterward. Early-bird seats are $49 while they last.
- Massachusetts fits a dense old-city core, a belt of former mill towns, two very different coastlines, and a mountain corner into a short drive.
- Much of the state's independent business sits on named main streets rather than highway strips: Shrewsbury Street in Worcester, Union Square in Somerville, Centre Street in Jamaica Plain.
- The Route 128 and I-495 rings decide how far a Massachusetts customer will drive before picking someone closer to home.
- Cape and Berkshire owners plan around a season. Boston and Cambridge owners plan around students arriving and leaving.
Which cities in Massachusetts have a seminar page?
- Boston, MA · Coming soon. Pre-register to hear first.
- Worcester, MA · Coming soon. Pre-register to hear first.
What happens on the night in Massachusetts?
Nobody presents at you. The tools go up on the screen, the prompts get typed in front of the room, and the results show up unedited so you can judge them yourself. Bring a laptop and use your own business as the test case.
The list of jobs is deliberately unglamorous: answering the questions customers keep asking, following up so a lead does not sit and cool, turning rough notes into a quote or a proposal, batching out marketing, trimming the scheduling exchange, and getting through routine writing such as summaries, checklists, instructions, and standard documents.
Mike Filsaime has been building companies for twenty-five years, Kartra, Groove, WebinarJam, and EverWebinar among them, and he teaches this the way he would explain it to a friend across a counter. Live, in plain words, with the screen visible.
How business actually works in Massachusetts
Massachusetts business does not look the same twice. In Boston the storefront is narrow and the rent is high, so a Roslindale bakery or an Allston repair shop lives on regulars and word of mouth. Cambridge and Somerville squares fill with tiny operations, one and two people deep, competing for the same foot traffic.
Head out along the Pike and the picture changes to Worcester's Canal District and the old mill blocks of Lowell, Lawrence, and Fall River, where cheaper space lets shops, gyms, studios, and small trades set up with room to work. Customers there drive, compare, and then stay loyal for years.
On the Cape and the islands, and out in the Berkshires, most of the year's money arrives in a rush and the quiet months go to catching up on whatever got skipped. Salem, Gloucester, and Newburyport run a similar rhythm on the North Shore. Everywhere in the state the bottleneck is identical: one or two people doing the answering, quoting, posting, and paperwork on top of the actual work.
How Massachusetts businesses use AI right now
A Union Square restaurant drafts a week of posts and the answer to every reservation question in one sitting. A Dorchester plumbing outfit dictates what it found under a sink and gets a written estimate back to edit. An Andover law office turns a long call into a summary and a list of next steps.
A Pittsfield gym writes its renewal emails as a batch. A Hyannis rental manager stops trading six messages to set a walkthrough time. A Worcester accountant produces the client instructions she has typed a hundred times, once, then reuses them.
A New Bedford repair shop keeps follow-up alive on quotes that went quiet. A Cambridge nonprofit turns meeting notes into minutes. A solo seller in Beverly writes listings between packing orders. What stays with the owner is pricing, hard conversations, and anything going out publicly with the business name on it.
What do Massachusetts attendees take home?
- Turn a phone call into a written record. A long call leaves you with nothing written down. Talk it through once afterward and AI gives you back a summary, the decisions, and the next steps. A Worcester office or a Salem studio ends the day with notes instead of a vague memory.
- Batch the marketing instead of scrambling nightly. Sitting down at nine at night to write a post is how marketing stops happening. In one session you can produce a run of emails, captions, and a simple offer, then schedule them. A Berkshires season or a September student rush gets written before it arrives.
- Send the estimate the same day you look at the job. Rough notes from a site visit turn into a clean written estimate that you price yourself. The Dorchester basement you looked at in the morning gets a number in the afternoon, in words a customer can actually follow.
- Stop losing the leads that went quiet. A lot of lost work is somebody who never got a second message. AI tracks who is waiting, drafts the nudge, and keeps the wording yours. Nothing depends on you remembering a name from three weeks ago.
- Set times in one exchange. Scheduling eats a startling share of a week. AI reads the thread, offers times, confirms in writing, and sends the reminder, which keeps a two-person shop from running a switchboard.
- Keep the wrong work away from it. AI does not get pricing, and it does not get the call with a furious customer. Anything carrying your name in public gets human eyes first. The evening is specific about where that 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 Massachusetts ask about the seminar?
Will the Massachusetts seminar make sense if I have never touched AI before?
That is who it is written for. Everything is in plain English, typed live on screen, with no coding and no jargon. You are not expected to have used any of these tools before you walk in.
Is this really for ordinary Massachusetts businesses, or is it aimed at Boston tech companies?
Ordinary businesses, every kind of them. Trades, restaurants, shops, salons, gyms, cleaners, landscapers, agents, accountants, law and dental offices, nonprofits, agencies, online sellers, and solo operators all sit in the same room, because the work AI helps with is the same work in all of them.
What does the Massachusetts evening cost, and is there a guarantee?
Seats are $49 early-bird while available. If you attend and it is not right for you, say so before leaving the room and the registration fee is refunded.
Do I need to buy software or sign up for something after the Massachusetts seminar?
No. There is no course, no subscription, and no required purchase afterward. You leave with what was demonstrated and the ability to repeat it.
When will Boston, Worcester, or Springfield dates be announced?
Massachusetts dates are still being scheduled. Pre-registering puts you first in line for the announcement and holds the $49 early-bird price.
Where do the Massachusetts dates sit in the wider program?
Every Massachusetts 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. 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.