The Brief
by The Craft of AI.
Bi-weekly long-form deep dives on how named operator-CEOs are actually shipping AI in their businesses. The decisions they made, what it cost them, and what you should steal. One story per issue.
Recent Issues
Every Kinsale Employee Has an AI License. The Moat Was Built 15 Years Before.
Kinsale writes $1.6B a year in policies the rest of the insurance market refused. AI didn't build that moat — sixteen years of underwriting discipline did. The bots just enforce it.
Most CEOs Buy AI Licenses. WD-40 Bought Operating Margin.
Steve Brass spent 31 years inside WD-40 before taking the CEO seat in September 2022. He took a public position on the customer outcome the company had been failing — and the work he refused to keep imposing on his planners — before he procured a single AI tool. The licenses were the same. The order was different. The receipt is 100 basis points of gross margin expansion in Q2 fiscal 2026.
Randy Wood Is Turning a 70-Year-Old Sprinkler Company Into a Subscription Business — Because a Broken Gearbox in July Is a Farmer Who Doesn't Call in November
A $620M irrigation equipment maker in Omaha is quietly pivoting to Tech-as-a-Service — and the reason isn't recurring revenue. It's that the AI earns its keep preventing the one service call that loses you the customer.
The NYT Just Got Played. Here's the Part They Missed.
A $1.8B AI telehealth profile, an FDA warning letter everyone ignored, and what operators should actually take from the Medvi story.
Klarna Replaced 700 Customer Service Agents With AI. Then It Hired Them Back. Both Decisions Were Right.
Sebastian Siemiatkowski made the loudest AI-replaces-humans bet in fintech history — and then publicly reversed it. Operators should study both moves, because neither was a mistake.
Warby Parker's Virtual Try-On Is the Most Misunderstood AI Project in Mid-Market Retail
Neil Blumenthal and Dave Gilboa built the thing everyone calls 'the AI feature.' The AI feature is not the point. The data it generates is the whole company now.
Sweetgreen Promised 100% Robot Kitchens. Quietly, They Settled on 50%. Here's Why That Number Matters More Than the Original One.
Jonathan Neman made the loudest automation commitment in mid-market restaurants — then walked it back to a floor, not a ceiling. Operators should study the walk-back, not the headline.
The Founder Who Came Out of Retirement, Killed 80 Spreadsheets, and Spent $60M on a Warehouse Before He Touched a Chatbot
Steve Schlecht's Duluth Trading sequence is a masterclass in what operators should do first — and it starts with the least exciting AI project in the building.
Ariat Cut Warehouse Steps From 40,000 a Day to 7,000 — And Never Once Called It an 'AI Strategy'
Beth Cross has been running the same playbook for 36 years: pick one worker, measure their hardest day, remove it. In 2026 the tool is agentic robotics. The method is the part to steal.
Rehrig Pacific's AI Read 14,000 Pages of Its Own Binders Before It Ever Talked to a Customer
A 112-year-old plastics manufacturer in Los Angeles made the contrarian first AI move of 2025.
Weekly Scanner Archive
Earlier weekly-scanner format. The Brief is now bi-weekly long-form — these remain for historical context.
AI Budgets Get Real
The era of blank-check AI spending is over — ROI frameworks finally arrive
The AI Integration Tax Comes Due
Companies discover that connecting AI to real systems is harder than building the AI itself
The Enterprise AI Talent War Heats Up
Everyone wants AI operators — nobody's training them
The Model Commoditization Tipping Point
When the models stop mattering, what you build around them is all that's left
The Week AI Agents Got Real Jobs
Enterprise deployments move from pilot to payroll — and the governance gap widens
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