CEO AI Literacy Program
Learn AI without an audience.
Private, one-on-one upskilling for CEOs — comfort, confidence, and real fluency with AI, from bare-bones basics to the most advanced topics, without your team, your board, or anyone else in the room.
Start privately with PaulWhy private
You're not supposed to already know this. Nobody told you that.
Every other AI education path puts you in a room with the people you lead — your team, your board, your peers. That's exactly backwards for a CEO. You need the room where the question “what's a token?” doesn't cost you any authority, and where “I don't understand this yet” is just the starting line, not a confession.
Thirteen sessions, one relationship
Bare-bones basics to the most advanced topics — in private.
Order flexes around what's actually happening in your business this quarter, but this is the full arc: from your first prompt to a working agent, a rehearsed board, and a standing practice you keep for as long as you want it.
Phase one
Foundations
Get hands-on with the tools and the technology before anything else.
First Contact
Copilot, ChatGPT, Claude, Perplexity, Gemini — or whatever your company already pays for. We sit down together and use the tools, live, on real problems from your actual week, until the interface stops being the obstacle and becomes just another app on your desktop.
Zero to Business
The 30-Minute Startup, run on you. You rebuild your own company from a blank page — problem, landing page, and investor pitch deck — in one working session, so you feel in your hands what your newest hire with an AI subscription can now do in an afternoon.
AI, From First Principles
Every stage of AI, in depth — rule-based systems through agentic AI — with the honest verdict on each one: what it's actually good for, what it was never going to solve, and where your own company sits on that timeline today versus where your competitors already are.
Phase two
Lead & decide
Turn fluency into faster, better calls — and a shorter, sharper priority list.
How Not to Blow It
The transformation playbook, and — more usefully — the graveyard. What separates the rollouts that actually stick from the expensive pilots that quietly die in month four, told through the specific failure patterns Paul has watched take down otherwise-smart leadership teams.
The Faster Yes
How to use AI to see your own numbers faster and more clearly than anyone in the room — a working session on turning a messy data question into a confident decision in minutes instead of the week it takes to wait for a deck.
The Short List
Every AI opportunity in your business, scored and ranked — and then cut down, ruthlessly, to the three your team should actually be working on this quarter. Leave with the prioritized list, not a 40-item backlog nobody will ever finish.
Phase three
See around corners
Rehearse the room, watch the market, and know exactly what could go wrong.
Dress Rehearsal for the Boardroom
We research and model your actual board of directors as AI agents, then rehearse your next hard conversation with them before you ever walk into the room — so you already know who moves first, who needs convincing, and where the pushback is going to come from.
The Watchtower
Build a standing set of scheduled AI agents that watch your competitors, your market, and your own public footprint on a recurring cadence — so competitive intelligence becomes something that arrives in your inbox, not something you remember to go look for once a quarter.
The $225 Million Decision
A live, high-stakes simulation with $225,000,000 on the line and an AI system you're told to trust. Context engineering risk doesn't show up as a warning label — it shows up out of nowhere, mid-decision, and this session is where you feel that for the first time somewhere it's safe to get it wrong.
Know Your Blast Radius
Every category of AI risk that should be on your radar — inference, output, training-data, agentic, and non-technical — mapped to what's actually in your business today, so you can tell a genuine exposure from a hypothetical one your general counsel read about online.
Phase four
Build & sustain
Ship something real, connect it to your systems, and keep the fluency current.
Your First Hire Who Never Sleeps
You build a working AI agent, end to end, against a complete set of mock data modeled on your exact company systems — no IT ticket, no security review, no real customer data anywhere near it. By the end you've deployed something real, on a practice company that looks exactly like yours.
Plugging In
Connect your own systems — email, calendar, drive, CRM, whatever you actually run on — to the AI tools you now trust, so the answers you get stop being generic and start being grounded in your company's real information.
Office Hours, On the Calendar
Standing 30-minute sessions, weekly or biweekly, for as long as you want them. Bring whatever came up since the last one — a vendor pitch you don't trust, a board question you can't answer yet, a tool your team wants that you can't evaluate alone. This is the relationship that keeps the fluency current.
Proof, not vibes
How you'll know it's actually working.
This program is measured the same way the full AI Transformation Program is — short-, medium-, and long-term metrics defined before you start, so “it's going well” is never just a feeling.
Short-term
Weeks 1–12
Learning module completion
AI usage — every tool, not just one
Survey responses on comfort and confidence
Quality of prompts and context provided
Culture signals around AI
Habit change — is it becoming default behavior
Medium-term
Months 3–12
Number of AI agents deployed
Human-in-the-loop vs. human-on-the-loop vs. human-out-of-the-loop agents
AI usage across every tool and system, not a single vendor
Long-term
Year 1+
ROI
System time
Revenue per employee
EBIT per employee
Employee satisfaction
Culture
When you're ready
This is the on-ramp, not the whole road.
Most CEOs start here privately, build their own conviction, and then bring Paul in for the board and executive ignition session — the entry point to the full 14-part AI Transformation Program for the whole company.
Frequently asked
Questions from CEOs.
Is this really private — just me and Paul?
Yes. No direct reports, no board members, no note-takers, unless you specifically invite someone. The entire point is a room where you can ask the basic question you'd never ask in front of your own team.
What if I genuinely don't know anything about AI yet?
That is exactly who this is built for. Session one assumes nothing. If you already have some fluency, we start further in — the curriculum meets you wherever you actually are, not wherever you're supposed to be by now.
How is this different from the AI Transformation Program?
This is the individual on-ramp. The AI Transformation Program is the company-wide, board-to-front-line rollout. Many CEOs start here privately, build their own fluency and conviction first, then sponsor the board and executive ignition session and the full 14-part program for the organization.
What's the format and cadence?
Sessions run virtually or in person, roughly weekly or biweekly, 30 to 60 minutes each, scheduled around your calendar rather than a cohort's. Order is flexible — we sequence around what's actually in front of you this quarter.
Can my leadership team or board join later?
Yes. This program is designed to work as a private starting point, not a dead end. When you're ready, the same relationship extends into the board and C-suite ignition session, and from there into the full AI Transformation Program.
Ask the question you can't ask your team.
One private conversation with Paul to see where you actually stand, and what the first session should cover.
Start privately with Paul