Maryland Owners, Winning With AI Is Almost Here
Owners drive in from Baltimore rowhouse storefronts, the Annapolis docks, Carroll Creek in Frederick, and the far side of the Bay Bridge. Different trades, the same pile of unanswered messages. Bring a laptop.
What is the seminar in Maryland?
Winning With AI is a live evening seminar for Maryland business owners of every type, from contractors and restaurants to salons, gyms, dental and medical offices, agencies, nonprofits, online sellers, and one-person operations. It shows how to put AI on the everyday work: answering customers, following up so leads do not go cold, turning notes into quotes and proposals, producing marketing, reducing scheduling back-and-forth, and clearing routine written admin. Mike Filsaime teaches it in plain English, with no coding and no prior experience needed, at $49 early-bird while available.
- Maryland packs Atlantic beaches, a working harbor, open farmland, and Appalachian foothills into a couple of hours of driving.
- Independent business in the state clusters along three corridors: I-95 between Baltimore and the DC line, US 50 out to the Eastern Shore, and I-70 west toward Frederick and Hagerstown.
- Baltimore trades on neighborhood main streets, Hampden, Canton, Highlandtown, Federal Hill, each with its own set of small operators.
- Bay Bridge traffic and the Ocean City season shape how many Maryland owners plan staffing and cash flow across the year.
Which cities in Maryland have a seminar page?
- Annapolis, MD · Coming soon. Pre-register to hear first.
- Baltimore, MD · Coming soon. Pre-register to hear first.
What happens on the night in Maryland?
Nothing about the evening is a preview of the future. The tools open on a screen, the prompts get typed where you can read them, and the output lands raw so you can decide whether it is any good. You work along on your own laptop with your own business as the example.
The jobs covered are the ordinary ones every Maryland business has: answering the questions customers keep asking, following up so a lead does not go cold, turning rough notes into a quote or proposal, producing marketing in batches, cutting the scheduling back-and-forth, and getting through routine writing like summaries, checklists, instructions, and standard documents.
The teacher is Mike Filsaime, twenty-five years into building companies, Groove and Kartra among them along with WebinarJam and EverWebinar. He explains it without jargon and works every example live in the room. There is no course or subscription waiting at the end.
How business actually works in Maryland
Maryland is small on the map and wildly different from one end to the other. Around Baltimore the commerce sits on rowhouse blocks: corner restaurants, body shops, salons, dental and medical offices, and trades working on old housing stock. Cross into Montgomery and Prince George's and the customer base turns into commuters, so service businesses get timed around people who leave early and get home late.
Annapolis works on a clock set by the water and the legislative session. Frederick and Hagerstown pull from a wide rural catchment, so a shop there serves people who drive twenty or thirty minutes and expect to be remembered when they call back. Past the Bay Bridge, Salisbury, Easton, and the Ocean City strip stack most of the year into a few months.
Out west around Cumberland and Deep Creek, weekend visitors and local trades carry the load. What all of it shares is thin staffing. The owner is also the one answering the phone, writing the estimate, and posting to social at night. That is the pressure point AI reaches first.
How Maryland businesses use AI right now
A Hampden salon has AI draft answers to the same five questions that arrive overnight, so nobody opens to a full inbox. A Canton contractor talks through a walkthrough into his phone and gets a written estimate back to price himself. A Frederick accountant turns a messy client email into a checklist of what is still missing.
An Annapolis rental operator writes a season of posts and emails in one sitting instead of scrambling every week. A Silver Spring dental office trims the scheduling exchange down to a single message. A Salisbury landscaping crew keeps proposals moving out on the day the site visit happens.
A Towson nonprofit turns board notes into minutes and a follow-up list. A one-person online seller in Rockville drafts listings and buyer replies between shipments. None of this needs new systems running the business. It works alongside what is already there, and pricing stays with the person who owns the pricing.
What do Maryland attendees take home?
- Answer the overnight questions before the day starts. Most of what arrives after hours is a version of the same handful of questions. AI drafts the replies from the way you already answer them, so you approve and send rather than retype. A Baltimore shop or a Bethesda office opens the day with an inbox that is already handled.
- Get a quote out while the job is still fresh. You walk a job in Towson, talk through what you saw into your phone, and the notes come back as a written estimate with your own numbers in it. You check the pricing, because pricing is your call, and it goes out instead of sitting until the weekend.
- Keep follow-up from quietly dying. Leads go cold in the gap between a first conversation and a second one. AI drafts the check-in, keeps track of who has not heard back, and writes it in your words. The work of remembering stops being yours.
- Write a month of marketing in one sitting. Instead of scratching out a post the night before, you produce a batch: emails, social captions, a simple offer, all in one session. An Ocean City season or a Frederick spring rush can be written out before it starts.
- Cut the scheduling back-and-forth. Six messages to find a time is normal and it does not have to be. AI reads the thread, proposes times, confirms in writing, and sends the reminder, so nobody on your team plays calendar tag.
- Know what to leave alone. Some things do not belong anywhere near AI. What you charge is judgment and stays yours. A tense call with an upset customer stays yours. Anything public enough to affect your reputation in Annapolis or Hampden gets read by a person before it goes out.
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.
What do people in Maryland ask about the seminar?
Is the Maryland seminar only for tech-minded businesses, or can any owner follow it?
Any owner. The room mixes contractors, restaurants, salons, gyms, repair crews, landscapers, cleaners, real estate agents, accountants, law offices, dental and medical offices, nonprofits, online sellers, agencies, and owners who do the whole job alone. Nothing on the agenda assumes coding or previous AI use.
What will I be able to do with AI by the time I leave the Maryland event?
Draft customer replies, write follow-up that does not depend on your memory, turn notes into a quote, produce marketing in batches, settle a time without a long thread, and get routine documents written. You will also know which parts of your business to keep away from it.
How much does the Maryland seminar cost, and what happens if it is not useful to me?
It is $49 early-bird while that pricing lasts. Attend, and if it is not right for you, say so before you leave the room and the registration fee is refunded.
Do I have to buy a course or a subscription after the Maryland seminar?
No. The evening is the whole thing. Everything shown uses tools you can reach on your own, with no upsell waiting afterward.
When is a Baltimore, Annapolis, or Frederick date going to be announced?
No Maryland date is set yet. Pre-register and you hear first, with the $49 early-bird rate held for you.
Where do the Maryland dates sit in the wider program?
Every Maryland 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.