Secondary · 1-on-1 Role Coaching
Monthly coaching for the operator’s side of AI.
6-month minimum commitment. Continues month-to-month after.
Senior operators, agency principals, founder-leads who want a structured monthly coaching relationship rather than booking ad hoc calls.
Two 90-minute sessions per month. Async support between. Structured around your role and the specific things you’re trying to get better at — building, scoping, shipping with AI as a serious collaborator.
When monthly coaching is the right shape.
The Brain Lifeline is for one-off questions. The Personal Brain Installis for a productized deployment. There’s a third shape: a structured ongoing coaching relationship — someone who knows your work, checks in on a cadence, helps you think through the harder calls before you have to make them alone.
The Coaching Retainer is for that shape. Two 90-minute sessions per month, scheduled in advance, structured around your specific role. Async support between sessions for the smaller questions. Six-month minimum because coaching compounds — the value of session 8 is mostly the prior seven sessions of accumulated context.
Calibrated for senior people whose work is significantly AI-leveraged and who want to be intentional about how that leverage compounds. Builders. Agency owners. Founders. Senior ICs in technical roles. If you’re just getting started with AI, the Open Cohort is the right shape, not this.
What the monthly structure looks like
Four touchpoints per month, four per quarter.
Session 1 · mid-month
90 minutes. Working session. We pick the most live problem and work through it. Agenda set by you the week before, refined by me, held loosely.
Session 2 · end of month
90 minutes. Half working, half reflective. Close the loop on what landed and what didn't. Look forward to next month's live problem.
Async between
Text, voice memo, screen recording. One business day response, substantively. For questions that don't need a meeting but benefit from a thoughtful written reply.
Quarterly review
2 hours every three months. Zoom out: what's changed about your work, where the leverage is now, what to focus on next quarter.
“The cadence creates the structure. The fact that there's a session in two weeks changes how you work in the next two weeks.”
Coaching compounds
Six-month minimum, month-to-month after.
$1,500/mo. Scope on the Diagnostic Call. The first three months are ramp; the value lands hardest months 4–12 as accumulated context builds.
What we work on
Common engagement arcs.
Personal AI workflow
Shipping work with AI as collaborator. Which workflows benefit from which tools, how to structure inputs, when to escalate to a brain install.
Scoping client AI work
For agency owners. Better diagnostic frameworks, sharper scoping conversations, more confidence in what to charge. Work through real client situations.
Leading an internal rollout
In charge of "AI" at your company with no peer above you who knows what they're doing. A peer who's been there to talk through architecture + change management + political calls.
Career positioning
Your work is AI-leveraged. Be intentional about how you communicate that — what you build publicly, what you publish, what the next role looks like.
Macro-trend sense-making
The AI landscape is moving fast. A peer to help you read what matters and what doesn't, what the next 12 months probably look like.
Why six months.
Two reasons. The first is that coaching value compounds — by month three or four, the conversations get materially better because we have shared context, shared vocabulary, and working memory. Engagements shorter than six months mostly cost themselves in the ramp.
The second is that the cadence creates the structure. The fact that there’s a session in two weeks changes how you work in the next two weeks. People do work to “have something to talk about.” That structure is half the coaching. A 3-month relationship doesn’t generate the same forcing function because the end is visible from the start.
After six months, the retainer continues month-to-month with no further commitment. Most clients who go past month six stay for at least a year. Some end at month seven once the patterns are internalized. Both are right outcomes — the structure is calibrated for the work, not for keeping you on the meter.
Common questions
Asked, answered.
How is this different from the Brain Lifeline?
The Lifeline is one-hour, scoped to a single question, no structure between calls. The Coaching Retainer is monthly with structured sessions plus async between, building on accumulated shared context. If you’d use the Lifeline 3+ times a year, the Retainer is more honest math — same dollars roughly, much more compound value.
Can I combine this with a Personal Brain Install?
Yes — common combo. The Install lands the system; the Retainer keeps you sharp on using it. Some Retainer clients did the Install first; some are doing the Install in month 3 of the Retainer because the coaching helped them see what they actually needed.
What if I miss a session?
Reschedule within the month. Sessions don’t carry over month-to-month — the cadence is the value. If you miss two sessions in a month, the lost session converts to async credit for that month rather than rolling forward.
What if I want to pause for a few months?
You can pause once during the six-month commit for up to 30 days (life happens). Past that, you finish the commit or end the engagement.
Can my partner / co-founder join?
Sessions are 1-on-1 by design. If you want a second person on calls, that’s a different shape (probably the Strategy Advisory). For one-off sessions where it makes sense, we can bring a second person in case-by-case.
Adjacent paths
Where this connects.
Start with the Diagnostic Call.
The Diagnostic Call commits to nothing. If this install isn’t the right shape for your work, I’ll tell you what is.
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