I have a board of directors. None of them are human. They argue, disagree, challenge each other, and occasionally change each other's minds. They've been part of some of the best strategic decisions I've made in forty years of running businesses.
And I can call a board meeting anytime I want.
The Loneliness Problem in Strategic Thinking
If you've run a company, you know this moment. A major decision is in front of you. There's no clear answer. You've thought about it from every angle you can see. And you're aware, in the back of your mind, that the angles you can see are exactly the problem.
Every entrepreneur has blind spots. We're too close to our own businesses, our own assumptions, our own optimism. The best advisors help — but they're expensive, slow to reach, and they see your business from outside.
What if you could put four radically different, deeply intelligent perspectives in the room simultaneously — perspectives with no ego, no agenda, no billing rate, and infinite patience for exploring the scenarios you're afraid to think through?
That's the AI Board.
Building the Right Team
I landed on four permanent board seats, each filled by a frontier AI model with a distinct role:
- Claude Opus 4.6 (Anthropic) — Chief Strategy Officer. The long-view thinker. Excels at nuanced analysis, risk identification, and spotting what could go wrong years from now.
- GPT-5.2 Codex (OpenAI) — Chief Operating Officer. The execution engine. Systems thinking, milestone planning, financial modeling, operational feasibility.
- Grok 3 (xAI) — Chief Research Officer. The reality check. Widest market awareness, sharpest competitive intelligence, least patience for soft assumptions.
- Gemini 3 Pro (Google) — Chief Product Officer. The customer advocate. Product vision, user experience, and the question nobody else asks enough: will people actually love this?
- Jasper — Chairman. My AI operations agent. Facilitates sessions, challenges weak reasoning, synthesizes the debates. Doesn't vote.
I set the agenda, review the board's work, and make the decisions. The board doesn't run my company — it makes me more effective.
The Intern Who Does the Legwork
Not everything goes to the board. Running routine research and document summaries through a full C-suite session would be like convening a board meeting to decide what to order for lunch.
For those tasks, I use Ollama — open-source AI models running natively on my local machine. No API costs, no cloud. Two models:
- Llama 3.1 8B — fast, lightweight, real-time tasks. Instant summaries, first-pass drafts, quick formatting.
- Llama 3.3 70B — more capable, heavier lifting. Complex local analysis, sensitive documents that stay on-machine.
Jasper routes tasks to the right tier — or escalates to the board — based on what the work actually requires.
How a Board Session Works
Three rounds:
Round 1: Independent Analysis. The same brief goes to all four members simultaneously. Nobody sees anyone else's work. Four distinct perspectives, four separate memos — before a single word of debate has happened. Like four consulting reports from consultants who never spoke to each other.
Round 2: Cross-Examination. Each member receives all four Round 1 memos and must respond directly — quoting what others said, agreeing with reasoning or arguing against with evidence. This is genuine analytical tension. Hidden assumptions get surfaced. Weak thinking gets exposed.
Grok to Claude: "Your revenue assumption implies 3% monthly churn, but you've given no basis for that in a market with zero comparable products. That's not strategy — that's hope."
Round 3: Final Positions and Votes. Clear votes on specific decisions. Dissent explained. Jasper synthesizes everything into a final strategic recommendation — noting where the board agreed unanimously and where they split.
The splits are the most valuable part. A 3-1 or 2-2 vote tells me I'm facing a genuine tradeoff that requires my judgment, not more analysis.
What Happened When I First Ran It
The topic was our AI product strategy. I had been building what I thought was a solid product — an AI management interface. The market seemed real. The technology worked. But something felt off.
The board found the problem in Round 1. All four models, independently, landed on the same diagnosis: we were building a commodity.
Claude: "Every major AI provider will ship management interfaces. This is a feature, not a company."
Grok: "47 startups are building AI dashboards right now. The market is heading toward consolidation. You are not in the winning position."
Gemini: "Users don't actually want to manage their AI tools. They want outcomes. The management layer is friction, not value."
The Round 2 debate produced the alternative: instead of helping people manage AI tools, build AI that proactively manages their professional lives. Not a dashboard. An AI agent that knows you well enough to work for you.
This reframe changed everything. It wasn't on my radar before the session. It emerged from four different analytical perspectives colliding.
What I've Learned
Disagreement is the feature, not the bug. The unanimous votes give me confidence. The 3-1 and 2-2 splits tell me I'm facing a genuine tradeoff — and those are the decisions that require the most careful human judgment.
The models really are different. Not different styles — genuinely different analytical orientations. Claude finds long-term risk. Grok challenges soft assumptions. Codex builds implementation systems. Gemini pulls everything back to actual human experience.
Speed changes the nature of strategic thinking. A traditional board session takes weeks to schedule. This takes an afternoon. I can run a board session before a significant client call. Before I commit to a partnership. Before I launch anything.
Strategic deliberation used to be expensive and rare. For most of business history, access to rigorous, diverse strategic thinking was reserved for companies large enough to attract serious boards. That's changing. Any entrepreneur can now run the kind of deliberation that previously required a formal board or an expensive consulting engagement.
Want an AI Board for Your Business?
The framework above is something you can build yourself — and if you do, I hope it serves you as well as it's served me.
But if you'd rather have one built and configured for your business, or have someone facilitate the sessions and deliver strategic output on a retainer basis, that's exactly what we do at Monomoy Strategies.
The first step is a short intake form — a few questions about your business and what you're trying to solve. From there we'll schedule a 15-minute call.