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Thinking Out Loud

Observations on AI, technology, and strategy — from the things I'm building and the patterns I'm seeing.

The Problem With Perfect
AI Strategy
The Problem With Perfect
I asked ChatGPT to write a cover letter for a fictional job posting last week. It was flawless. Professional tone, action verbs, quantified achievements, keywords from the job description. I could have sent it immediately. So could ten thousand other people. This is the adequacy trap. AI makes it easy to achieve competence across every […]
AI-Powered Relationship Management
AI Strategy
AI-Powered Relationship Management
I opened Facebook and saw three birthdays I’d missed, two promotions I should have congratulated, and a message from someone I’d promised to introduce to a colleague four months ago. I’m not careless about relationships. I care. But caring isn’t enough when your network outgrows your memory. Most networking advice assumes your constraint is meeting […]
The Right Answer from Wrong Math
AI Strategy
The Right Answer from Wrong Math
ChatGPT calculates Net Promoter Score correctly about 70% of the time in my BYU classroom. The other 30%, it either miscategorizes responses or just makes up a number that sounds right. The dangerous part? Half the time it fails, it still lands on the correct answer through completely wrong reasoning. It’ll count 7s and 8s […]
Competitive Intelligence and Strategic Transparency
AI Strategy
Competitive Intelligence and Strategic Transparency
I was presenting a competitive intelligence system to a client’s executive team when the CEO stopped me mid-demo. “Wait. If we can monitor our competitors this way, can’t they monitor us?” Everyone went quiet. You could see the calculation happening. If intelligence is this easy to collect, maybe we should stop publishing so much. Lock […]
Stop Building What You Should Be Buying: The Economics of Workflow Automation
AI Strategy
Stop Building What You Should Be Buying: The Economics of Workflow Automation
Last month I watched a business owner spend three weekends building an inventory reconciliation workflow in Make. Beautiful architecture. Conditional logic. Error handling. API integrations to Square, QuickBooks, and Google Sheets. He showed me the flow diagram like a trophy. Then I asked what his time was worth. “Around $150 an hour.” I pulled up […]
Network Diagrams for Competitive Strategy
AI Strategy
Network Diagrams for Competitive Strategy
I’ve been carrying network diagrams into high-stakes conversations my entire career. Crime analysis, competitive intelligence, due diligence work. The visual shows patterns that spreadsheets bury: who’s connected to whom, who sits at the center of power, where the structural gaps create opportunity. Almost no one in business uses them. Most companies still analyze competition in […]
The Chatbot That Never Disagreed
AI Strategy
The Chatbot That Never Disagreed
A founder I know spent six weeks building a market entry strategy with ChatGPT. Every morning he’d refine the thesis, ask for risks, get thoughtful objections, address them in the next draft. By week six he had fifty polished slides and total confidence. When he showed me the deck, three things jumped out: a supplier-side […]
The Customization Tax Nobody Talks About
AI Strategy
The Customization Tax Nobody Talks About
The Customization Tax Nobody Talks About A mid-sized logistics company spent $400,000 on enterprise AI software last year. Great product. Proven ROI. Used by dozens of their competitors. Six months later, they wondered why their AI investment hadn’t created competitive advantage. The answer was simple: they’d paid for efficiency, not differentiation. Every one of their […]
The Most Expensive Question You Never Ask
AI Strategy
The Most Expensive Question You Never Ask
The Most Expensive Question You Never Ask A founder came to my office last month with a twelve-slide pitch deck. Beautiful design. Impressive revenue projections. Three different market opportunities, each requiring different capabilities, different partners, different brand positions. “Which one should I pursue?” he asked. Wrong question. The right question: “Which one am I actually […]