A Founder's Retreat, AI Officer Institute
Problem first. AI second. ROI always.
The Premise
We are in the 50/50 era. AI now handles roughly half the work of running a business, and that share grows every month. The founders who understand this are not just building more efficient companies. They are building a fundamentally different kind of company: one with near-zero marginal labor cost, extraordinary margin, and virtually no ceiling on scale.
The question is no longer whether AI can run your business. It already can. The question is whether you know how to design and instruct it.
That is what this retreat is for. On the first afternoon, we spend two hours on the framework, then two more hours working through your blueprint to map your Agent Org Chart and business plan. Over the next two days, you build it, in focused pods with engineers on site to handle configuration and keep you moving. You leave with a working agent stack: a company full of AI agents doing real work, ready to run.
The Case Study
One Person. One Model. One Year.
$401 Million. 16% Net Margin. Two Employees.
In 2024, Matthew Gallagher launched Medvi, a telehealth platform for GLP-1 weight-loss drugs. He used twelve AI tools. He had one employee, his brother. In 2025, Medvi did $401 million in revenue at 16.2% net margin. Hims and Hers does the same thing with 2,400 employees and nets 5.5%.
Gallagher did not build an AI company. He took an established business model, connecting patients with doctors and prescription fulfillment, and replaced every internal function with either an AI agent or an outsourced platform. Customer service: AI. Marketing content and ad creative: AI. Analytics and business intelligence: AI. The hard stuff, medical compliance, pharmacy networks, shipping, he outsourced to platforms that already had it solved.
He is not a developer. He is not a technical founder. He is an operator who learned how to design workflows, catalogue data, and write instructions for AI. Those three skills, applied to a proven market with an existing infrastructure stack, produced one of the most capital-efficient businesses ever built.
The Framework
The two hours are divided into two equal halves. The first hour covers the model: what you are building and why it works. The second hour covers the skills: the three foundational capabilities every founder in the 50/50 era needs to actually build it.
Hour One, The Model
1. The Three-Layer Company
Every AI-first company is built on three layers. The Infrastructure Layer is everything hard that someone else has already built, compliance, fulfillment, regulation, payments, logistics, licensing. Your job is not to build this. It is to identify the platforms that already have it solved and plug into them.
The Agent Layer is the intelligent middle of your company. Marketing, customer service, analytics, content creation, outreach, reporting. Every one of these functions gets an AI agent. The reframe is simple: you are still hiring. You are just hiring agents.
The Founder Layer is you. Strategy. Capital allocation. Expansion decisions. Key relationships. Anything that requires genuine judgment about where the company goes next. Your goal at this retreat is to shrink your own job description down to its irreducible core and hand the rest to agents.
2. Choosing Your Market
Gallagher did not invent a new category. He looked at a market that already existed and asked a different question: where is the middle layer still bloated with human labor? The market selection test for this framework has three criteria.
First, the market must be large and proven, you are not creating demand, you are capturing it. Second, there must be an infrastructure layer you can plug into. Third, the middle layer must be AI-replaceable: marketing, matching, customer success, content, analytics. If humans are currently doing those jobs in your target market, that is your opportunity.
For most EO members, the best market to look at first is the one they already know. The exercise is not finding a market. It is seeing your own market through this lens for the first time.
3. Mapping Your Agent Org Chart
This is the central exercise of Hour One. Every company, regardless of industry, has the same five core functions: Marketing, Customer Success, Operations, Finance, and Technology. For each function, you place it in one of three columns:
Platform, handled by an existing service. You pay for it, connect to it, do not manage it. Agent, handled by an AI agent you design and instruct. It runs autonomously, reports to you, and gets better over time. Founder, only you can do this. It requires your judgment, your relationships, or your authority.
By the end of this exercise, every person in the room has a one-page visual of their company built entirely of platforms and agents, with the founder at the top making decisions. This is your build plan for the next two days.
4. The Margin Machine
The numbers are the point. Gallagher hit 16.2% net margin at $401 million in revenue. That is $65 million in profit, with two people. The traditional comparable, Hims and Hers with 2,400 employees, runs at 5.5%. That gap, roughly 11 margin points, is the agent premium.
High margin means you do not need to raise capital. You do not dilute. You do not answer to a board. You reinvest into marketing, grow the customer base, and the margin stays high because your cost structure does not scale with your revenue. That is the flywheel.
The target for companies built on this framework is 15% net margin from day one. Not as a long-term aspiration. As a design requirement.
Hour Two, The Skills
Knowing what to build is 50% of the game. The other 50% is knowing how to build it with AI, and that requires three specific capabilities that most founders have never been formally taught.
Foundational Skill 1, Workflow Design
Before you can automate anything, you have to see it clearly. Workflow design is the discipline of mapping a business process, every step, every decision point, every handoff, so precisely that an AI agent can execute it without guessing.
Most founders carry their workflows in their heads. The problem is that AI cannot read your mind. It can only follow explicit instructions on a structured path. Workflow design is the translation layer between how you think and how your agents operate.
In this block, you learn to map any business process using a simple structure: trigger, steps, decision rules, outputs, and exceptions. You practice on your own Agent Org Chart, taking one of the functions you mapped in Hour One and designing the workflow that will govern it. You leave with one complete workflow ready to hand to an agent.
Foundational Skill 2, Data Cataloguing
Agents are only as good as the data they can access. Data cataloguing is the practice of identifying, organizing, and labeling the information your agents need to do their jobs, your customer records, your product details, your pricing rules, your brand voice, your policies, your historical performance data.
Most businesses have this information scattered across email threads, spreadsheets, Notion docs, old slide decks, and the founder's memory. Before your agents can work, that information needs to be organized, named, and made accessible. Data cataloguing is not a technical task. It is an organizational one.
In this block, you learn a simple cataloguing framework: what data each agent needs, where that data currently lives, what format it needs to be in, and how to keep it current. You leave with a data catalogue outline for your first two agents, ready to populate during the build days.
Foundational Skill 3, Generating AI Instructions
This is the most important skill in the 50/50 era, and the one almost nobody has been formally taught. Writing effective AI instructions, what most people call prompts but what AI Officers call agent instructions, is not a technical skill. It is a communication skill. And like all communication skills, it can be learned, practiced, and mastered.
An agent instruction is a complete briefing for a role. It tells the agent who it is, what it does, what it knows, what decisions it makes autonomously, what it escalates to you, and what success looks like. A great agent instruction reads like the best job description you have ever written: specific, unambiguous, and impossible to misinterpret.
In this block, you learn the AI Officer instruction framework: Role, Context, Task, Rules, Output Format, and Escalation Criteria. You write your first full agent instruction, test it live, refine it based on the output, and leave with a working instruction ready to deploy in the build.
The Schedule
- Starts 2:00 PM, half day
- Session 1 (2 hrs): framework, three-layer company, market selection, Agent Org Chart, margin machine, and the three foundational skills
- Session 2 (2 hrs): each founder works the blueprint with their pod engineer
- Goal: Agent Org Chart finalised, business plan drafted, first workflows mapped
- Evening: light social at the Sailing Club
- Full build day, four 2-hour sessions
- Founders work in pods, one engineer to every three founders
- By end of day every founder has at least one live agent
- Standard is not polished, it is working
- Evening: social at Skylight
- Morning, half day
- Final build session to refine, polish, and complete anything outstanding
- Engineers on-site through the morning for last-minute configuration
- After lunch: Awards, a celebration of what was built
- Every founder walks out with a live agent doing real work
Investment
Registration closes May 30.
- Hotel (2 nights)
- All sessions
- Food and drinks
- On-site engineers
- Sailing Club social
- Skylight social
What You Walk Away With
The Foundation of the Company, Built During the Retreat
- A completed Agent Org Chart, every function of their company mapped to a platform, an agent, or the founder
- A data catalogue outline, the reference library their agents will draw from every time they act
- At least two working agent instructions, written, tested, and refined against live output
- At least one working agent stack, live, connected to real data, executing real tasks
- A margin model, showing what the business looks like at target with near-zero labor cost
The Success Condition
You came in running a business. You leave designing a company.
The difference is not philosophical. It is structural. A business scales by hiring people. A company built on this framework scales by deploying agents, and the cost of a new agent is a fraction of the cost of a new hire, with none of the management overhead.
In five years, there will be two kinds of operators: those who learned to lead with AI, and those who got left behind by someone who did. The founders who go through this retreat will not be wondering which kind they are.
Problem first. AI second. ROI always.
Facilitation Notes
For Facilitators
AI Officer Institute, The Infinite Leverage Blueprint, Problem first. AI second. ROI always.