Operator Mastermind
A small standing room of operators putting AI into real businesses.
What it is
A closed room with continuity. Same people, month over month.
This is not a Slack community, a cohort course, or a panel series. It is a small group of owners and senior operators who meet monthly for ninety minutes, share what they are actually building, and stay in the room long enough for the conversation to compound.
We run the room. We bring the framing, the cases, and the discipline. Members bring the work. The point is to think clearly out loud with people who are doing the same thing, and to leave each session with a decision or a built thing that would not have happened alone.
What a month looks like
- 01
Pre-read circulated.
A short brief from one member or from us. Read before the session, not during it.
- 02
90-minute working session.
One or two cases brought by members, worked in the room. Cameras on. No panel.
- 03
Two peer-pairs run between sessions.
Members are paired monthly to compare notes on a specific question. Thirty minutes, on the calendar.
- 04
Monthly 1:1 with us.
A standing call — strategic question, awkward decision, sanity check. Whatever the month asks for.
- 05
Library kept current.
Working prompts, workflows, and decision memos contributed by the room. Members keep what they bring and what others share.
Who is in the room
Owners doing $5M–$100M, senior operators inside larger orgs, agency leads who run on AI internally. Vendor-neutral. No recruiters, no consultants pitching for work, no investors looking for deal flow.
The bar is the operating distance — how close you are to the work AI actually touches. A founder-CEO of a $20M services business and a VP of operations at a $200M manufacturer can both be the right fit. A board member who wants to "stay informed" is not.
What members get
- 01
Faster decisions on AI investments.
A peer review on the build, the buy, or the do-nothing — before the money goes out.
- 02
A working library from peers.
Prompts, workflows, and decision memos contributed by the room and kept current.
- 03
A place for the strategic question.
The kind of question that does not fit a board meeting and is too consequential for a Slack channel.
What we expect
Show up. Share the work. Keep the room confidential. Members who go quiet for two months get a one-off check-in from us, and after that the seat reopens. The room only works when the people in it are actually using it.
How it compares
| Operator Mastermind | Cohort Course | Slack / Community | |
|---|---|---|---|
| Cohort size | 8–12 | 20–100 | Hundreds+ |
| Cadence | Monthly working session + 1:1 | Weekly for 6–12 weeks | Anytime / async |
| Continuity | 12-month minimum | Ends when the cohort ends | No structure |
| Who runs it | Practitioners alongside members | Course instructor | Volunteer mods |
| Best for | Operators with skin in the game | Skill-up on a topic | Loose peer signal |
Frequently asked
- How do you select members?
- Short application plus a 30-minute call. We optimize for fit and operating distance, not seniority.
- What does it cost?
- Annual membership, quoted on the call. Pricing is tiered by company size.
- Are sessions recorded?
- No. Recordings change what people share.
- Can my partner or co-founder also join?
- One seat per company, by design. We can run a separate conversation for partner pairs if it makes sense.
- How is this different from your other engagements?
- Audit, implementation, and training are scoped projects. The mastermind is a standing room. Many members have done a project with us first.