Advance your Annapolis business with AI
A live evening with Mike Filsaime teaches Annapolis and Chesapeake Bay area leaders how to use AI in government, maritime, tourism, and professional services. Learn real workflows, skip the hype, and implement this week.
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

What is the seminar in Annapolis, MD?
Winning With AI comes to Annapolis as an evening seminar teaching government, maritime, and business leaders how to adopt practical artificial intelligence. Learn workflows that defense contractors, tourism businesses, and state agencies are already running.
- Format: Live, in-person evening seminar with real Q&A and business examples from your region
- Audience: Annapolis government officials, maritime business leaders, tourism operators, and entrepreneurs
- Focus: Government workflows, maritime operations, tourism management, business growth using AI
- Teaching style: Clear instruction from someone who built successful companies and understands operations
- Pre-register: Spots are limited; early registrants get priority when the date is confirmed
The evening in Annapolis, explained
This seminar brings practical AI training to Annapolis for a single evening focused on regional business leaders. You see which AI tools government, maritime, and tourism operations use effectively. Mike teaches from real experience, not academic theory.
The content covers procurement, citizen communication, maritime logistics, tourism marketing, and operations management. You learn which AI applications deliver results in government and defense contracting. You leave knowing your next step.
You don't just gather ideas; you leave with a specific plan. You know which AI tool to implement first, how to introduce it to your organization, and what to measure to confirm it's working.
Is AI worth it for a small business in Annapolis, Maryland?
Annapolis and the Chesapeake Bay region operate at a specific pace. Government agencies manage citizen communication and compliance. Maritime operations coordinate complex logistics. Tourism businesses depend on seasonal workflows. AI improves efficiency in all these domains, directly impacting operations and budgets.
Organizations that move to AI first gain competitive advantage. When your agency or business uses AI more effectively than others in your space, you deliver better results with the same resources. That advantage compounds over time.
Your team wants to work with current technology and methods. When you're adopting AI strategically, your people see you're forward-thinking. That attracts talent and improves retention.
A practical AI seminar built for Annapolis businesses
Annapolis is home to the Naval Academy and a strong government and defense contracting sector. These organizations manage complex compliance, security, and documentation requirements. AI helps automate compliance tracking and document management without compromising security or quality. This fit is direct and immediate.
Maritime businesses on the Chesapeake Bay coordinate shipping, manage inventory, and handle customer communication. AI improves scheduling, tracks shipments, and manages customer follow-up automatically. These tools fit naturally into maritime operations.
Tourism is vital to Annapolis and the region. AI automates booking confirmations, seasonal marketing, and visitor communication. These workflows strengthen customer relationships while reducing administrative burden.
What Annapolis attendees walk away with
- Government workflows automated. Learn how AI processes permits, manages citizen communication, and handles compliance tracking automatically.
- Maritime operations improved. Discover how AI optimizes shipping schedules, tracks inventory, and forecasts demand in your maritime operations.
- Compliance and security. See how AI helps you maintain compliance and security protocols without manual verification of every detail.
- Tourism and marketing. Learn how AI manages customer communication, personalized recommendations, and seasonal marketing.
- Administrative efficiency. Understand how AI reduces time your staff spends on documentation, scheduling, and routine reporting.
- Regional competitive edge. See how adopting AI strategically puts your Chesapeake region organization ahead of others in your field.
Who the Annapolis seminar is for
Annapolis government and agency leaders
Learn how AI improves citizen services, compliance tracking, and administrative efficiency.
- Automate permit processing and compliance tracking
- Improve citizen communication and responsiveness
- Reduce administrative overhead on agency staff
Maritime and logistics operators
Discover AI workflows that optimize scheduling, inventory, and shipment management.
- Forecast demand and optimize shipping schedules
- Track inventory and manage logistics automatically
- Improve communication with customers and partners
Tourism and hospitality leaders
Learn how AI handles customer communication, booking management, and seasonal marketing.
- Automate booking confirmations and follow-ups
- Personalize customer recommendations
- Manage seasonal promotions and staffing
A live seminar vs. free videos vs. an online course
| This live seminar | Free online videos | Self-paced AI course | |
|---|---|---|---|
| Format | Live training in Annapolis where you interact with the instructor and see local business examples. | Scattered online tutorials with no connection to government or maritime workflows. | Self-paced videos; you watch alone and figure out how to apply it to your organization. |
| Relevance to Annapolis | Focused on government, maritime, defense contracting, and tourism businesses specific to the region. | Generic content; most targets individual creators or tech companies, not government or maritime. | Broad modules; hard to find content relevant to government or maritime operations. |
| Instructor experience | Mike Filsaime built Groove, Kartra, WebinarJam, EverWebinar; understands operations and scale. | Instructors vary; many lack real organizational or operations management experience. | Instructors often without experience in government or maritime contexts. |
| Network and community | Meet other government, maritime, and business leaders in the Annapolis area; build professional connections. | No community; isolated learning from your screen. | Discussion boards exist but lack depth or real peer professional connections. |
| Organizational readiness | Leave with a specific implementation plan tailored to government or maritime organizational needs. | You gather scattered ideas but lack a coherent organizational strategy. | Generic curriculum; unclear how to implement in a government or maritime context. |
What is Annapolis, MD actually like?
Annapolis is a city of structured thinking and institutional excellence. Government, military, and maritime traditions run deep. The business culture emphasizes precision, compliance, and long-term thinking. AI adoption fits naturally into that environment.
The Chesapeake Bay region attracts educated professionals across government, defense, maritime, and tourism. Your workforce can learn and apply new tools quickly. That capability means faster adoption and better results.
Annapolis leaders value stability and proven methods. They want to know what works, what the cost is, and what the risks are. This seminar gives them that clarity, so they can make informed decisions about AI adoption.
How Annapolis businesses are using AI right now
Government agencies in Annapolis use AI to process citizen requests, organize permits, and manage compliance documentation. Defense contracting firms use AI to manage procurement processes, track security requirements, and coordinate with subcontractors. Maritime businesses use AI to forecast demand, optimize shipping schedules, and manage inventory. These workflows improve efficiency across government and commercial operations in the region.
Tourism organizations use AI to respond to visitor inquiries, send personalized recommendations, and manage seasonal promotions. Administrative teams use AI to organize records, flag compliance issues, and create reports. Operations coordinators use AI to manage schedules across locations or departments. The pattern is consistent: AI handles routine administrative work so people focus on strategy and relationships.
Headlined by Mike Filsaime
The Annapolis session is taught by Mike Filsaime, who spent 25 years building digital businesses before he started teaching AI. He built Groove, Kartra, WebinarJam, and EverWebinar, which means the workflows in this room come from someone who had to make them work in his own companies first.
He is a pioneer in AI and online business, and his reputation rests on plain English. No jargon, no theory for its own sake, no assumption that you already know what a model or a prompt is. If you can describe the job you want done, you can follow what he shows you.
In Annapolis he works through the moves in front of the room, live, with time for questions from the people actually sitting there. You see the workflow built rather than described, which is the part that does not survive a recording.
People who have seen this in action
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.
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.
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.
Coming soon 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
Annapolis questions and answers
Is this AI seminar appropriate for government leaders in Annapolis?
Yes. The content covers compliance automation, citizen communication, and administrative efficiency. You'll see direct applications to government operations.
Do I need a technical background to attend?
No. The seminar teaches AI as an organizational tool. If you manage operations or a team, you have what you need.
How does this apply to maritime and logistics businesses?
You'll learn how AI optimizes shipping, forecasts demand, manages inventory, and handles customer communication automatically.
What about security and compliance requirements?
The seminar covers how AI helps you maintain compliance and security protocols without sacrificing the oversight you need.
Who teaches the Annapolis seminar?
Mike Filsaime teaches every session. He built Groove, Kartra, WebinarJam, and EverWebinar and has 25 years in business.
When will this come to Annapolis?
We're building attendance from Annapolis and Chesapeake Bay area leaders now. Pre-register to secure your spot and help set the date.
Can I bring colleagues or team members?
Yes. Many organizational leaders bring colleagues so your whole team learns the same strategies and can implement together.
What is the ticket price?
Pricing details will be shared as we finalize the event date. Pre-register now for early pricing options.
How do I pre-register for the Annapolis event?
Click the pre-register button on this page. We'll send you event details as the date gets confirmed.
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