The Lawman’s Mastermind 2026 is a two-day working session for law firm owners who want to grow their practices. The October 2026 session runs October 15-16 in St. Augustine, Florida. This preview covers the format, the cost, who should attend, how to get there, and how to register.
What Is the Lawman’s Mastermind?
The Lawman’s Mastermind, also called the Umansky mastermind, is a two-day working session for law firm owners hosted by William “The Lawman” Umansky, founder and managing partner of The Umansky Law Firm in Orlando, Florida. The format centers on a “Hot Seat” working session rather than a lineup of conference lectures. Attendees bring real business problems to the group and work through them together.
Umansky founded The Umansky Law Firm, a criminal defense and injury practice in Orlando, in 1999. He has more than thirty years of experience and graduated from the University of Florida College of Law, where he served on the trial team. Before going into private practice, he tried more than a hundred cases as a prosecutor in Brevard County and served as City Prosecutor for Orlando. He is a co-author of the Amazon best-selling law practice book Tiger Tactics and hosts a podcast for lawyers called The Lawman’s Lounge.
That background matters for a working session. Umansky has built and run a firm through the same hiring, intake, and growth decisions attendees face, so the event centers on his experience rather than a slate of outside speakers.
The event is for firm owners who are actively scaling, not associates or first-year attorneys. Most legal conferences are built around keynotes and panels, where you sit and absorb. This one inverts that. The day focuses on your firm and the firms in the room, so the value comes from peer problem-solving, not passive listening.
When & Where: October 15–16, 2026 · St. Augustine
The October 2026 Lawman’s Mastermind takes place October 15-16, 2026, at the Hyatt in St. Augustine, Florida. If you have been searching for a law firm mastermind in St. Augustine, this is the one. The table below lists the confirmed details from the official landing page.
| Details | Information |
| Dates | October 15 to 16, 2026 |
| Location | Hyatt, St. Augustine, Florida |
| Format | Two-day working session with a Hot Seat format |
| Investment | $799 per attendee (full-day session plus networking dinner) |
| Capacity | Limited seats |
| Registration | Secure Stripe checkout |
What Does the Lawman’s Mastermind Cost?
The Lawman’s Mastermind costs $799 per attendee. That covers the full-day mastermind session and the opening networking dinner. It does not cover hotel rooms, travel, or meals outside the dinner, so budget for those separately. Payment runs through secure Stripe checkout.
For a full day of direct input from firm owners at a similar stage, plus a dinner to build those relationships, $799 is a modest figure for the hours of peer advice involved.
How the Lawman’s Mastermind “Hot Seat” Format Actually Works
The Lawman’s Mastermind uses a Hot Seat format. Each attendee takes a turn presenting their biggest firm challenge to the group, and the group works together to find the root cause and propose solutions. You take the seat and bring your ideas, your problems, and the real state of your business.
This format is not for the passive. You are expected to contribute, to share real numbers, and to take direct feedback. The event page is blunt about it: the Hot Seat is not for the weak or the lazy, and there is no room for egos.
The problems people bring are the ones that stall a firm: hiring, marketing spend, case intake, partner disputes, and growth plateaus. The day would involve digging into your practice issues and leaving with actionable steps you can put to work. The event opens the evening before with a networking dinner, which gives you a chance to meet the room before anyone takes a seat.
The format works because the people in the room have usually already solved the problem you are stuck on. A firm owner one revenue tier ahead of you has lived through your bottleneck and can tell you what worked and what wasted their time. That kind of specific, lived answer is hard to get from a keynote or a book, and that’s why the session is structured the way it is.
One honest disqualifier: if you are not ready to share real numbers and be honest about what isn’t working, this isn’t the event for you.
Hennessey Digital at the October 2026 Mastermind
Jason Hennessey, founder and CEO of Hennessey Digital, will attend the October 2026 Lawman’s Mastermind in St. Augustine.
Hennessey Digital is a digital marketing agency that works with law firms and has run legal campaigns since 2015. In that time, it has become a 6x Inc. 5000 honoree and a Financial Times fastest-growing company in America. Its founder, Jason Hennessey, has been studying the Google algorithm since 2001 and focuses on law firm SEO, the practice of optimizing a firm’s website and online presence so it ranks higher in search results and in AI search tools when potential clients look for legal help.
Jason Hennessey wrote the book on law firm SEO, and he leads a team that has grown more than 1,000 firms, so a specialist runs your account, not a trainee. The agency’s own research spans more than 1,300 firms and 15,000 legal sites, including a lead-form response study that shows where firms lose the cases they already paid for. That work has generated more than $1 billion in leads and verdicts for law firms. The strategy is grounded in that primary research, not hunches.
For firm owners in the room, that is a useful voice to have at the table. Marketing spend and client intake are two of the challenges people bring to the Hot Seat, and both depend on search visibility. Having someone who works on law firm search every day, in a session built on candid problem-solving, gives attendees a direct line on a problem many of them are trying to fix.
Featured Speakers & Attendees
The Lawman’s Mastermind is host-led by William Umansky, with additional input promised from keynote experts closer to the event. The landing page lists learning from keynote experts as part of the program, but no specific speaker names are published as of this writing.
The format puts peer-to-peer working sessions ahead of traditional keynote speakers. That is the point of the Hot Seat: the room does the work. The real draw is the attendee pool, a small group of firm owners at similar stages of scaling. Because the group is small, every attendee gets a turn in the seat.
Check the landing page and the Umansky team’s channels close to the event for any confirmed speaker additions.
What You’ll Walk Away With
The event sets out three things attendees leave with:
- Expert connections and advice. Working relationships with high-performing law firm owners, many at a similar or slightly higher revenue tier than you.
- A personalized strategy and roadmap. A clear plan of action for your firm, aimed at the bottleneck you brought to the table and shaped by peer input.
- Modern blueprints to scale and dominate. Tactical frameworks that other firm owners have used to grow past specific plateaus.
The connections tend to outlast the two days. A relationship with an owner who has already cleared the plateau you are facing is worth returning to long after the session ends. The roadmap is the piece you act on, and its value shows up in what you put into practice over the following weeks. What you implement is on you.
How to Get to St. Augustine
The St. Augustine Hyatt is easiest to reach through Jacksonville International Airport (JAX), roughly 50 miles north. The drive south takes about 45 minutes to an hour on Interstate 95, depending on traffic. Two other airports are within driving range if the fares work better for you.
| Airport | Distance to St. Augustine | Approximate drive |
| Jacksonville International (JAX) | About 50 miles | 45 minutes to 1 hour |
| Daytona Beach International (DAB) | About 60 miles | 1 hour to 1 hour 15 minutes |
| Orlando International (MCO) | About 110 miles | 2 hours to 2 hours 30 minutes |
JAX is the closest major airport and the simplest route for most attendees. Daytona Beach and Orlando both work if a flight into one is cheaper or more convenient, with the trade-off of a longer drive. Confirm your own drive time with a maps app on a weekday before you travel, since I-95 traffic shifts through the day.
A rental car is the practical choice. St. Augustine has limited public transit, and a car gives you flexibility for the dinner, the hotel, and anything you want to see while you are in town. Uber and Lyft both serve the JAX-to-St. Augustine route; fares generally run from $70 to $140, depending on timing and service, so confirm the current rate in the app before you rely on it. If you drive, the Hyatt charges $27.50 plus tax per night for parking, limited to one vehicle per room, and the fee covers full-service valet. Trailers, RVs, buses, and oversized vehicles are not allowed.
Where to Stay
The Lawman’s Mastermind takes place at the Hyatt in St. Augustine, which is also the recommended hotel for attendees. Booking a room there keeps you close to the session and the dinner. Book early, since seats and rooms both go quickly.
Things to Do in St. Augustine
St. Augustine was founded in 1565 and is the oldest continuously inhabited European-founded city in the United States. It is an easy place to add a day before or after the event. Walk the old city, see the fort, and spend time by the water.
Who Should Attend
The Lawman’s Mastermind is designed for law firm owners actively scaling their practice, not associates, first-year solos, or attendees looking for a passive conference experience. The split below shows who gets the most out of the room and who does not.
| Attend if you’re | This isn’t for you if you’re |
| A law firm owner with at least two years of ownership behind you | An associate or first-year solo, or not yet a firm owner |
| Actively hitting a growth plateau you can’t diagnose alone | Not facing a specific problem you need help working through |
| Ready to share real revenue numbers, staffing structure, and marketing spend with peers | Not willing to share real numbers about your firm |
| Willing to give candid advice to other firm owners, not just receive it | Looking only to take advice, not contribute it |
| In a practice area where firm growth is possible, such as personal injury, mass torts, criminal defense, or family law | Looking for a passive conference experience |
If the left column describes you, the room will be full of people solving the same problems you are. If the right column does, the format won’t pay off.
Frequently Asked Questions
These are the questions attendees ask most often before registering for the Lawman’s Mastermind.
What Is The Lawman’s Mastermind 2026?
It is a two-day working session for law firm owners, hosted by William “The Lawman” Umansky. Attendees take turns in a Hot Seat, presenting a real firm challenge for the group to help solve. The October 2026 session runs October 15-16 in St. Augustine, Florida.
How much does the Lawman’s Mastermind cost?
It costs $799 per attendee, paid through secure Stripe checkout. That covers the full-day session and the opening networking dinner.
Is the Lawman’s Mastermind worth it for solo attorneys?
It depends on where you are. The event is built for firm owners who are actively scaling and ready to share real numbers. A solo owner with at least two years of ownership who fits that description can get a lot out of it, since the Hot Seat does not care about firm size, only about whether you come with a real problem and real numbers. A first-year solo or someone looking for a passive experience is not the target attendee.
What Is the Hot Seat Format at The Lawman’s Mastermind?
Each attendee takes a turn presenting their biggest firm challenge to the whole group. The group then works to identify the root cause and propose solutions. It calls for honest numbers and candid feedback, in both directions.
What’s included in the $799 Registration?
The $799 covers the full-day mastermind session and the networking dinner the evening before. It does not include hotel rooms, travel, or meals outside the dinner.
Are there other Lawman’s Mastermind dates in 2026 or 2027?
The landing page lists two 2026 sessions: a May Mastermind on May 14 to 15 at the Grand Bohemian Hotel, and the October Mastermind on October 15 to 16 at the St. Augustine Hyatt. Check the official page for any dates announced beyond those.
How to Register
Registration for the October 15 to 16, 2026 Lawman’s Mastermind is open through secure Stripe checkout at $799 per attendee, and seats are limited.
Book your hotel room separately. The $799 covers the event only, not your accommodations, so reserve your room at the St. Augustine Hyatt as soon as you register. Because capacity is capped to keep every attendee a turn in the seat, the seats tend to fill up before the date. For the cancellation and refund policy, contact the Umansky team directly before you book, since the organizers set those terms.