WinningWithAI.com - Live AI seminars with Mike Filsaime

Winning With AI, an Annapolis Evening in Person

How many messages does it take you to book one appointment? How long has that quote been sitting half finished? When did anything last go out to your customer list? Those three questions are the whole agenda for this evening in Annapolis. Pre-register and you learn the date first.

Coming soon to Annapolis, MD. The date and venue are not set yet. Pre-register to be the first alerted when they are.

Pre-register for the seminar in Annapolis

Annapolis, Maryland, one of the cities on the live AI seminar tour

What is the seminar in Annapolis, MD?

Winning With AI is one live, in person evening headed for Annapolis, and every kind of small business around the Severn is welcome, owners, managers, and the people doing the work. No industry is the target. What the night covers is the writing that every business drags along: answers to customer questions, follow up that keeps a lead from cooling off, notes turned into quotes, proposals, or estimates, marketing produced in batches, less back and forth over scheduling, and the routine documents you keep retyping. It is just as clear about the work that must stay human, meaning what you charge, the conversation with an unhappy customer, and anything that goes out in public under your name. Mike Filsaime runs the room. Early bird seats are $49 while they last, and the registration fee is refunded if you attend and say before leaving that it was not for you. Nobody codes, nobody uses jargon, no experience is needed, and there is nothing to buy when it ends. The Annapolis date is not set, which is why pre-registration is the step available today.

  • A single Annapolis evening, live in the room, with no recording to catch later.
  • Open to any small business from Eastport to Parole to Cape St. Claire.
  • $49 early bird while seats last, refunded if you tell us before leaving that it missed.
  • Every word in plain English, and nothing to install ahead of time.
  • No product pitch at the end, no course, and no monthly anything.
  • No Annapolis date yet. The pre-register list hears it before it goes public.

What does the evening in Annapolis actually cover?

Nobody reads slides at you. Every step happens live on a screen in an Annapolis room, at a pace where you can copy the wording down.

The material is ordinary writing. The inquiry that shows up during Saturday dinner. The customer from two weeks ago still waiting on a call. A page of notes that owes somebody a proposal. A quarter of emails and posts nobody has written. The five message thread about what time works. The same instructions, typed again from scratch.

The evening spends just as long on the other side. Pricing is a judgment call and stays one. So does the difficult conversation. So does anything Annapolis customers will read with your name attached. This is a drafting tool and the night says so plainly.

Is AI worth it for a small business in Annapolis, Maryland?

A seat is $49 early bird while they last. Sit through the evening, and if it was not right, say so before you leave and the registration fee is refunded.

Interest in Annapolis is not the problem. The calendar is. Route 50 turns a short errand into ninety minutes on a summer Friday. Boat show week rearranges everybody's schedule. Paperwork slides to nine at night because the day belonged to customers.

This evening lifts that written load and puts it down somewhere better, leaving every human decision alone. You leave with steps written out and no homework.

Why is this AI seminar built for Annapolis businesses?

The room is not divided up by trade. A shop on Main Street, a crew crossing the Spa Creek bridge to Eastport, an office off Riva Road, one evening for all of them.

A deck builder working Admiral Heights. A crab house near City Dock. A salon in West Annapolis. A landscaper covering Arnold and Cape St. Claire. A two person tax office in Parole. A gym on Forest Drive. A cleaning company running Bay Ridge. A dental office near Jennifer Road. A nonprofit downtown. An agent listing across the South River in Edgewater. A canvas and repair shop off Bay Ridge Avenue. Somebody packing orders from a garage on Annapolis Neck. Their paperwork does not differ.

So the filter for what gets shown is simple. If a step only helps one type of business, it stays out of the evening.

What do Annapolis attendees walk away with?

  • Answer before they call the next name. An inquiry that waits until Monday is usually an inquiry that went elsewhere. Prepared answers go out the same evening.
  • Follow up that does not need reminding. Most quotes die from silence rather than price. You build the follow up once and then it runs on its own.
  • Site notes turned into a proposal. What you jotted down on the boat or the job becomes a document the customer can read, in your wording, without a late night.
  • Batch the marketing nobody has time for. A quarter of emails and posts gets drafted in one sitting, then trimmed until it sounds like your shop.
  • One message instead of five. Booking a time should not take a whole thread. The shorter version gets built on screen in front of you.
  • Write the standard documents once. Checklists, instructions, summaries, the form you rebuild monthly. Each one gets made properly a single time.
  • Where the tool has to stop. Pricing, upset customers, anything published under your name. The line gets drawn out loud and explained.

Who is the Annapolis seminar for?

What annapolis area owners get out of the Annapolis evening

Waterfront storefront or a truck and a phone.

  • Get the typing off your plate
  • Handle more customers with the same team
  • Leave with a first step for Monday

What managers running the schedule get out of the Annapolis evening

You know which tasks eat the week.

  • Stop rebuilding the same documents
  • Keep quality, lose the keystrokes
  • Take home steps the staff can use

What single person businesses get out of the Annapolis evening

There is nobody else to hand it to.

  • Reply while customers are deciding
  • Never lose a lead to a busy Friday
  • Get your evenings back

How does a live seminar compare with free videos and an online course?

This live seminarFree online videosSelf-paced AI course
SettingOne Annapolis evening among local ownersA screen by yourself at midnightWeeks of videos on your own time
FitEvery small business around the SevernWhatever a feed decided to showAimed at a nationwide list
Getting answersAsk in the room and hear it immediatelyType it under the video and waitEmail support and hope
How much is shownThe whole workflow, beginning to endTrimmed for watch timeRecorded before the tools shifted
When it endsNothing to buy, nothing to unsubscribe fromYou are on your ownBilled again next month

What is Annapolis, MD actually like?

Annapolis sits where the Severn meets the Chesapeake, with Eastport across the creek, Parole out along the highway, and Route 50 running the length of it toward the Bay Bridge.

Everything here bends around the season and the water. Summer weekends fill the streets and the parking. Winter empties them. A trip across the South River and back can take most of an afternoon in July. That makes anything you can finish in writing, from a phone at the dock, worth more here than in a place you can drive across in ten minutes.

That reality shapes the whole evening. Nothing demonstrated requires more than the phone and computer you already own.

How Annapolis businesses are using AI right now

This is not a look ahead at something coming. Businesses around Anne Arundel County are doing versions of it now, mostly without anyone technical on staff.

A dock and deck outfit stopped writing proposals at night, because measurements get spoken into a phone on site and come back written in the owner's own voice for one read and a send. A shop in West Annapolis that posted at random now builds a season of emails and posts in a single afternoon. A two person office that rewrote the same client packet weekly wrote it once and shelved it. A repair shop in Eastport keeps written answers to its most common questions ready before the next call comes in.

Every case looks alike. The typing disappeared, the judgment did not. Prices, tense conversations, and anything public still belong to the owner.

Who teaches the Annapolis seminar?

Twenty five years of building companies sits behind what Mike Filsaime teaches. Groove, Kartra, WebinarJam, and EverWebinar came out of that period, and they are tools small businesses use to run the ordinary day.

His whole method is plain speech. No abbreviations, no assumed vocabulary, no pretending the room already knows the words. He would rather open the tool and type the real thing on screen than describe what it might produce.

In Annapolis he pulls the sort of unfinished pile an owner near the water has waiting, and he works it through in front of everyone instead of showing a polished result.

What do people who have seen this say about it?

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.
Marnie, Wing Girl Method
Thank you for your incredible knowledge and insight. It made a powerful impact. I don't take anyone's time lightly, least of all someone with your level of marketing genius.
Tony Robbins, Entrepreneur & Author
He'll not only make it simple, he'll make it very profitable.
Rich Schefren, Strategic Profits
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.
Eric Berman, Founder & CEO, Brandetize

When is the seminar coming to Annapolis?

We have not set the Annapolis 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 Annapolis

What do people in Annapolis ask about the seminar?

Has the Annapolis date been announced?

Not yet. Pre-registration is open on this page, and that list gets the Annapolis date and location ahead of the public, with early bird pricing held while seats last.

Which part of Annapolis will host it?

The venue is still being settled. It will be somewhere with real parking and a reasonable drive from Eastport, Parole, Arnold, and Edgewater, and pre-registered people receive the address first.

Does the Annapolis seminar only suit certain industries?

No. It is written for whoever fills the room: contractors, shops, restaurants, salons, gyms, repair crews, landscapers, cleaners, real estate agents, accountants, law offices, dental and medical offices, nonprofits, online sellers, agencies, and businesses of one. The shared ground is paperwork.

What is the price of an Annapolis seat?

Early bird seats are $49 while they last. Come, and if it does not fit your business, say so before leaving the room and the registration fee is refunded.

I have never used any of these tools, can I still come to Annapolis?

Yes. Nothing on screen is code and no jargon gets used. Email and a phone are the only experience the evening assumes.

What gets taught during the Annapolis evening?

Customer replies, follow up before a lead goes cold, notes into quotes and proposals, marketing written in batches, fewer messages to set a time, and the routine written admin. A clear part of the night covers what to keep away from the tools: pricing, hard conversations, and anything reputational.

Who is running the Annapolis room?

Mike Filsaime. He spent 25 years building companies, Groove, Kartra, WebinarJam, and EverWebinar among them, and he runs the Annapolis examples in real time.

Can two of us come from the same Annapolis business?

Yes. Owners often bring the person who handles the inbox, since the setup goes faster when two people watched it happen.

Is there an upsell after the Annapolis seminar?

None. No course, no membership, no coaching offer. The evening is the whole thing.

Where does the Annapolis evening sit in the wider program?

The Annapolis room is one stop on Winning With AI with Mike Filsaime, 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 Maryland cities have a seminar page?

All Maryland cities | Every seminar city by state | AI for small business | Is an AI seminar worth it? | Who teaches it | Find a seminar near you