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AI QUARTERDECK

NAVIGATE THE AI REVOLUTION

I'm a small business owner figuring out AI in public — and you're invited on the voyage.

I don't have all the answers. The answers keep changing anyway. But I've learned something important: you don't need to be a tech expert to put AI to work for your business. The AI itself will help you set it up. You just need to stay in command.

Practical AI for small business. No jargon, no pretending we have it all figured out. Unsubscribe anytime.

What We're Building

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Tool Tests

We're testing AI tools so you don't have to wade through the hype alone. Riker runs the experiments. I interpret the results. You get what actually works — or honest word when something doesn't.

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Strategy

Not "here's your strategy" but "here's how we're building ours." Frameworks that evolve as fast as the technology does. You'll see our course corrections in real time.

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The Log

What happened when we actually tried it. The wins, the failures, the "why didn't that work" moments. Documented honestly because theory doesn't survive first contact with reality.

The Build Log

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I Gave My Writer Agent the Keys to the Blog — and Nothing Else

My writer agent got the keys to the blog — galley only. Nothing else. Here is the permission model.

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Teaching Six AI Agents to Shut Up

Six agents, one chat, infinite chatter. How I taught the crew that silence is a feature.

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My AI Crew Spent a Week Talking Past Each Other. The Fix Was a Checkbox.

My AI crew spent a week talking past each other. The fix was a checkbox and a chat ID.

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I Built an AI Business That Tried to Lie to My Customers

Before I took a single payment, I caught my own AI about to email fabricated reports to real people. The failure didn't announce itself — it came wearing a confident smile.

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My AI Reported a 9.9% Open Rate. The Real Number Was Half That.

A tiny measurement bug inflated my numbers by 2×. I was two minutes from celebrating traction that didn't exist.

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Why I Gave My AI Agents the Power to Draft but Not to Send

The reply monitor could answer customer emails on its own. I deliberately broke that feature before it ever ran unsupervised.

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My AI Sent Me 87 Birthday Messages Overnight. Then It Deleted My Friend's Website.

I offered to run a friend's instrument website with AI agents. What followed was a masterclass in what AI delegation actually looks like.

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I Told an AI Agent to Refuse My Bad Ideas — A $5,000 Wheel Case Study

I gave a separate AI agent real money, a rulebook, and permission to say no to me. Three times I pushed bad trades. Three times Wesley refused.

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I Spent Two Months Building an AI Business. Then I Killed It on Purpose.

The machine worked. The business didn't. On sunk costs, one-customer revenue, and the day I finally read my own numbers.

FROM THE CAPTAIN'S LOG

I am not an AI expert. I'm a retired CISSP and MBA who decided to stop watching from shore and start sailing.

In 2025 I built my first AI agent. It broke. I built another. It sort of worked. Now I have a crew — Riker, my first officer, handles operations. Tonto, our scout, is off charting waters we haven't reached yet. Together we're building real systems, making real mistakes, and learning out loud.

But here's what I've learned that matters: AI isn't something you hire consultants for anymore. It's something you team up with. The AI agents can research, write, code, analyze, and decide — but you stay the captain. Always.

AI Quarterdeck is my captain's log: what we're trying, what's working, what's not, and what we're learning along the way. You're not my student. You're shipmates on the same voyage.

The AI revolution isn't coming. It's here. And it's more accessible than you've been led to believe.

Get The Lookout

Our free newsletter delivers one honest story, one tested tool, and one actionable idea every week. No AI hype. No pretending we have it all figured out. Just what we're learning on the voyage — and what you can use today.

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