By Brett Kaufman. 8 years using relationships to build sales pipelines, from political fundraising to a 7 figure business to running matchmaking for two communities. Over 1,000 introductions facilitated.

How to start a mastermind group: define the one kind of deal maker it is for, invite a small group at the same stage who do not compete, and set a fixed rhythm with clear rules. Then treat the time between meetings as the product, because that is where intros, commitments and deals either happen or die.

Here is the scene. You keep having the same great dinner. Four operators, a lender, an independent sponsor. Someone always says “we should do this every month.” Nobody does. Six months later two of them did a deal together, and you heard about it secondhand. You were the one who put them at the same table.

I have never hosted a mastermind. I have been a founding member of Four Rooms Mastermind since 2022, and I run matchmaking for two communities. So I have seen the room from the member side and the matching side. Here is how I would start one for deal makers.

Who should a deal makers mastermind be for?

It should be for one kind of person at one stage, described in a sentence. “Owner operators who have closed one acquisition and want a second” works. “Entrepreneurs who want to grow” does not.

The test: every member should be able to help every other member with a real problem within a year. If a first time searcher and a fund partner sit in the same seat, one of them is teaching and one is learning, and the teacher leaves.

What format should you choose?

Pick the format from the job the group does. Here is the decision table I would use.

Format	Size	Rhythm	Good for	Watch out for
Hot seat circle	6 to 10	Monthly, 2 to 3 hours	Live deal problems, candid feedback	One member dominating
Facilitated peer group	12 to 16	Monthly, with a chair	Mature operators, steady accountability	Needs a strong facilitator
Dinner series	10 to 20	Every 6 to 8 weeks	Matching, new relationships	Feels social, not useful
Retreat model	20 to 60	2 to 4 times a year	Deep trust, bigger rooms	Long silence between events

The facilitated row is the model established groups use. Vistage describes its groups as 12 to 16 business leaders from non competing companies, facilitated by a Chair who is “part facilitator, part coach.” TIGER 21 asks members to commit to monthly meetings, and its groups have Chairs. You do not need their scale to borrow their structure: fixed size, fixed rhythm, someone accountable for the room.

How to start a mastermind group in 90 days

Here is the launch plan, step by step.

1. Week 1: write the one sentence. Who it is for, what stage, what they get. Share it with three people you would want in the room and listen to what they push back on.
2. Week 2: set the rules. Confidentiality, attendance, no pitching each other, and what happens to someone who misses twice. Write them down before anyone joins.
3. Weeks 3 to 4: invite by hand. Personal texts, not a sign up page. Start with people who already trust you, then ask each of them for one name.
4. Week 5: run an intake. For each member: what they do in one sentence, what they need in the next 90 days, and who they want to meet. This is the matching fuel.
5. Week 6: first meeting. Every member brings one live issue. Close with one commitment and one intro from each person.
6. Weeks 7 to 10: work the gap. Check every commitment. Make every promised intro, with a double opt in.
7. Week 12: second meeting, then review. Ask each member what they got from the first 90 days. Their answers tell you whether to grow, charge or change the format.

How do you match members so the room produces deals?

Match a need on one side to an ability on the other, then seat and brief them so they actually meet. Do not leave it to the cocktail hour. The full six step method is in mastermind member matchmaking, and for the seating itself, see how to seat a networking dinner.

What happens between meetings?

Between meetings is where a mastermind earns its renewals. The meeting creates commitments, promised intros and half started conversations. If nobody carries them, the next meeting starts from zero and members feel it.

Illustratively, a group of 10 that each make one commitment and one intro per meeting creates 20 open loops a month. Over a year that is 240 things someone has to remember. That is why most groups slowly turn into dinners. The day by day follow up plan is in mastermind follow up after a meeting.

Here is how I would run the gap

I would not run it from memory or a spreadsheet. I would run it from FRONT OF MIND, because the gap is exactly what it handles.

Capture every member and guest in seconds. Say a name and a sentence out loud, snap a badge or a business card, or take a selfie together, and it is filed under the event. Then the app opens on your 10 minutes for today, with a one line reason for each person: you met at an event days ago and never followed up, a follow up is due, or they are going cold.

Intros to make this week show up with dated proof on both sides. Ask Liala out loud, “who do I know that is an M&A advisor,” and get the right members with why. Every draft is a text style message, 40 words max. Nothing sends without your tap, and it learns from your edits.

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