Strategic
A pivot decision. Build vs. buy. Whether to launch the agent thing now or wait six months.
Vol. IV · 1:1 Coaching · MMXXVIDirect work · Tier IV
Bring the
question.
Two-hour minimum. No script, no slides, no deck theater. You bring the thing you’re stuck on. We figure the path together — on a call, in a doc, or both.
For founders launching with AI·Professionals making the pivot·Personal or org projects
Reserve a blockScoped 1:1 on the call
Pick the shape that fits.
Drop-in · 2-hour block — every block is scoped 1:1 on the call. Two-hour minimum.
What clients actually bringComposite, last 30 sessions
“I need to talk this out with someone who’s seen it before.”
Tactical
Vendor selection. Cost modeling. Pricing your own AI product. What metric to chase first.
Personal
Career sequencing. How to upgrade your skill stack without quitting. The conversation to have with your boss.
Org
Board prep. Team restructure. Skip-level conversations. The slide that's going to land in the wrong way.
Technical
Architecture review. Model choice. Where the seams are. Honest second opinion on the spec.
Open
What you're worried about and don't have anyone to ask. Off the record, by the way.
How a session runs
Four parts. Four hours, all in.
Before15 min
You send a one-pager. The question, the context, what good looks like to you. I read it the night before.
Call90 min
On Zoom. Recorded if you want. We work the actual problem on a shared doc. No deck. No throat-clearing.
After24 hrs
Written summary: what we decided, what to try, what to revisit. Yours to share or burn.
Follow14 days
One async pass on what's worked. Quick course-correct if something's off-track. Recorded if useful.
Before15 min
You send a one-pager. The question, the context, what good looks like to you. I read it the night before.
Call90 min
On Zoom. Recorded if you want. We work the actual problem on a shared doc. No deck. No throat-clearing.
After24 hrs
Written summary: what we decided, what to try, what to revisit. Yours to share or burn.
Follow14 days
One async pass on what's worked. Quick course-correct if something's off-track. Recorded if useful.
Voices
What they say after.
“I came in stuck on whether to build the agent internally or buy. We worked the unit economics live. Built. Shipped Q2.”
David ParkCTO · 80-person logistics SaaS
“Two hours saved me from making a board commitment I would have spent six months untangling. That's session time well spent.”
Erin WalshFounder · early-stage healthtech
“The follow-up note alone — written, no fluff — was worth the session. I forwarded the relevant chunks to my team verbatim.”
Jamal BrooksVP Product · mid-market fintech
Two doorsPick the one that fits.
The Plan bundles month one. 1:1 extends from there.
Most popular · 50% off through 2026-06-30
AI Transformation (Individual)
$2,500$1,250one-time
Your personal AI readiness plan.
- Personal readiness assessment
- Custom 90-day transformation plan
- Delivered within 5 business days
- 1st month of 1:1 Coaching included
- Extend via 1:1 Coaching tier
Start with the 5-min screener
Free screener first — Milton emails the plan checkout link if it's a fit.
Or already know it's a fit?
1:1 Coaching
Custom2 hr min
Work directly with Milton.
- Dedicated Milton hours
- Personal or organizational projects
- Extends Individual plans
- Email + async access
Org Transformation · Vol. V
Running a team or a whole org?
The personal path is built for founders and professionals. For org-wide transformation with executive alignment and rollout support, the consulting engagement is the right shape.
See the org consulting path →