Winning With AI Lands in Boston for One Night
Winning With AI is one live evening in Boston, open to owners of any small business. You watch the written work of a business get handled on screen: customer questions, follow up on leads, notes turned into quotes, marketing written in batches, scheduling, and routine admin. Early bird seats are $49. The Boston date is not announced yet, so pre-register and you hear it first.
Coming soon to Boston, MA. The date and venue are not set yet. Pre-register to be the first alerted when they are.
Pre-register for the seminar in Boston
What is the seminar in Boston, MA?
Winning With AI is a live, in person seminar coming to Boston, and it is open to small business owners of every type across the city and Greater Boston. A restaurant on Hanover Street, a contractor working out of Charlestown, a salon in Roslindale, a two person accounting office in Dorchester, a gym in Allston, a cleaning company under contract in Back Bay, a dental office in Brighton, a nonprofit in Roxbury, a real estate agent showing triple deckers in East Boston, and someone shipping orders alone from Jamaica Plain all belong in the same room. Mike Filsaime teaches the evening. He works through answering customer questions, following up on leads, turning notes into quotes and proposals, producing marketing in batches, cutting the back and forth over scheduling, and clearing routine written admin. He is just as direct about what to keep away from AI, which is pricing judgment, difficult customer conversations, and anything reputational. Early bird seats are $49 while they last, with a money back guarantee. There is no coding, no jargon, and no experience required, and nothing is sold at the end. The Boston date is not set, so pre-registration is open.
- One live evening in Boston, in person, start to finish in a single night.
- Open to small business owners of every type: shops, restaurants, contractors, salons, gyms, repair crews, landscapers, cleaners, real estate agents, accountants, law offices, dental and medical offices, nonprofits, online sellers, agencies, and one person operations.
- $49 early bird while seats last. Attend, and if it is not right for you, say so before leaving the room and the registration fee is refunded.
- Plain English the whole way. No coding, no jargon, and no prior experience.
- Nothing is sold at the end. No course, no subscription, no follow up program.
- The Boston date is not announced. Pre-register and you get the date, time, and venue before it goes public.
What does the evening in Boston actually cover?
Winning With AI is a working session, not a talk. Mike Filsaime builds each piece live on screen while the room watches and takes notes.
The subject is the written work every business carries: the question a customer sends before choosing you, the follow up on a lead that went quiet, site notes turned into an estimate, a month of emails and posts written in one sitting, the scheduling thread that runs eight messages, and the forms and instructions that get retyped over and over.
The evening also covers what to keep away from AI. Pricing judgment stays with you. So does the conversation with an angry customer, and anything published under your name. A tool can write a first draft, and you approve it.
Is AI worth it for a small business in Boston, Massachusetts?
A seat is $49 during early bird. Attend, and if it is not right for you, say so before you leave the room and the registration fee is refunded.
Boston does not hand a small business a quiet stretch to catch up on paperwork. Rent is high, parking is a fight, and the writing waits until nine at night. So an inquiry that arrives Monday sits until Thursday, an estimate gets typed after the kids are in bed, and nothing gets posted for two months.
One evening clears that stack off the desk. The parts that need a person stay with the person, and you leave with written notes and nothing owed.
Why is this AI seminar built for Boston businesses?
The room is built for Boston, not for one line of work. A tile setter on a South Boston condo job, a breakfast counter in Roslindale Village, a barber on Centre Street, a landscaper covering Milton and Hyde Park, a bookkeeping office in Fields Corner, a gym in Allston, a cleaning company working Back Bay buildings, a dental office in Brighton, a nonprofit in Roxbury, a real estate agent in East Boston, a repair shop on Dorchester Avenue, and an online seller packing orders in Jamaica Plain.
Ask any two of them what eats their time and the reply comes back in the same shape: quotes, replies, follow ups, and forms.
So every example shown has to travel across trades. If something only works for one kind of business, it does not go on the screen.
What do Boston attendees walk away with?
- Answer before anyone else does. Boston owners call three places and hire whoever gets back to them. Your common answers, written ahead of time, go out while you are still on a job.
- Follow up you set up once. A lead that went quiet last Tuesday is not gone. You watch a follow up sequence get built one time, then it keeps running while you are out.
- Notes at the curb, quote sent. Speak the job notes into your phone before you pull out of the space, then read back an estimate in your own wording instead of typing it at eleven.
- A month of marketing in one sitting. You give it one thing you know about your customers and get back a month of emails, posts, and offers to review in one sitting.
- End the eight message scheduling thread. Agreeing on a time is the most wasteful conversation in a small business, and worse when the job is across the river. There is a shorter way and you see it done live.
- What to keep away from it. Pricing judgment, an angry customer, and anything published with your name on it. The room hears this plainly, with the reasons.
Who is the Boston seminar for?
What owners across Boston and Greater Boston get out of the Boston evening
What you sell has no bearing on whether this fits.
- Get quotes out the same day they are asked for
- Handle more inquiries without adding staff
- Leave with a short written list of steps
What office managers and team leads get out of the Boston evening
You are usually first to notice where the day goes.
- Retire the forms nobody should be retyping
- Cut screen time without cutting output
- Hand your team steps they will actually use
What solo operators and two person shops get out of the Boston evening
Nobody else is going to pick up the writing.
- Keep replies going while you are on a job
- Stop losing leads to silence
- Get your nights back from admin
How does a live seminar compare with free videos and an online course?
| This live seminar | Free online videos | Self-paced AI course | |
|---|---|---|---|
| The setting | A Boston room of other owners | Your phone at midnight | A tab you stopped opening |
| Who it is for | Any small business, trade aside | Whoever got the clip | A national audience |
| Your own question | Asked out loud, handled that night | Left in a comment | Posted in a forum |
| What you leave with | Written steps, nothing owed | A watch history | A monthly charge |
What is Boston, MA actually like?
Boston is a compact city with a wide working region around it. Storefronts on Newbury Street run on foot traffic, crews based in Charlestown run on the gaps between calls, and offices in the Seaport often deal with customers they never meet in person.
The commute is the shared problem. Storrow Drive at five, the Mass Pike inbound, and the Sumner Tunnel backed up all cost the same hour. Snow emergencies end the workday early, and street cleaning costs a ticket if you forget. Anything that can be settled in writing is worth settling before anyone moves a truck.
So the evening stays on work you can put in place from a phone or a laptop before the end of the week, with no setup fee and nobody to call.
How Boston businesses are using AI right now
Plenty of Boston businesses already do this quietly, and most of the people doing it would never call the work technical.
An electrician running two vans out of Hyde Park used to write estimates at the kitchen table until eleven at night. Now he talks the job notes into his phone at the curb, reads back a quote in his own wording, and sends it before pulling away. A bakery in the North End keeps its common answers written and ready, so a message at ten at night gets a reply at ten at night. A shop manager in Allston wrote the opening checklist once and has not rewritten it since. A two person agency in Somerville put out a quarter of emails in one afternoon.
No consultant, no project, no line in the budget. One evening, and a decision about which few things are worth doing first.
Who teaches the Boston seminar?
Mike Filsaime teaches the evening. Over 25 years he has built companies including Groove, Kartra, WebinarJam, and EverWebinar.
His work is taking a business problem that looks complicated and cutting it into steps an owner can carry out without a technical background. No jargon, and no theory that stops at the door of a real business.
In Boston he walks through those steps in plain English, with time for questions from the room and examples you can set up yourself.
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 Boston?
We have not set the Boston 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 Boston
What do people in Boston ask about the seminar?
Has a Boston date been announced yet?
Not yet. Pre-registration comes first, and that list gets the Boston date, the start time, and the venue before any of it is public. Early bird pricing is held while seats last.
Where in Boston will the seminar be held?
The venue is not locked in. It will be somewhere reachable by T and by car from the neighborhoods and the closer suburbs, and pre-registered attendees get the address first.
Is the Boston seminar limited to 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 all sit in the same room, because the written work they carry is nearly identical.
What does a Boston 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 technical background for the Boston evening?
None. Nothing on screen is code and nothing said out loud is jargon. If you can use email and a phone, you can follow the whole night.
What is covered at the Boston seminar?
Answering the questions customers ask before they buy. Follow up so leads do not go cold. Turning notes into quotes, estimates, and proposals. Writing marketing in batches instead of one piece at a time. Ending the back and forth over scheduling. Clearing routine written admin. Then the other side of it: pricing judgment, difficult customer conversations, and anything reputational stay away from AI.
Who teaches the Boston evening?
Mike Filsaime, who has spent 25 years building companies such as Groove, Kartra, WebinarJam, and EverWebinar, and he runs the whole night in plain English.
Is anything sold after the Boston seminar?
No. There is no course, no subscription, and no program offered afterward. The evening ends, you keep your notes, and nothing further is asked of you.
Can I bring my office manager to the Boston evening?
Yes, and it is usually the better call. The person handling the phone, the quotes, or the calendar is the one who will put the steps to work.
Where does the Boston evening sit in the wider program?
The Boston 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. Same teacher, same demonstrations, same money-back guarantee in every city; the examples change to match the businesses in the room.
Which other Massachusetts cities have a seminar page?
All Massachusetts cities | Every seminar city by state | AI for small business | Is an AI seminar worth it? | Who teaches it | Find a seminar near you