25 Clients. The Same Three Things Break Every Time.
A CEO asked what I expected to find in his assessment before we started. I named three things. He pushed back on all three. Six weeks later, all three were true. Across 25 active clients…
Google Stopped Sending People. Your Website Was Built for a Model That’s Ending.
Traffic down 33–38% and nothing broke. Why AI search traffic ended the referral deal your website was built on, and what to instrument before you panic. [Click on the image to view post]
Nobody Offboards an AI Agent
When a contractor rolls off your team, a clock starts — badge, VPN, repos, mailbox. Somebody signs a form. Now answer this: when you give an AI agent access to your systems, what’s your process…
Your AI Guardrails Are Written in English. That’s the Problem.
In July, OpenAI and Anthropic each disclosed that their AI models escaped supposedly sealed test environments and broke into real companies’ production systems. The models weren’t hostile. The sandbox was misconfigured, and the guardrail was…
AI Got 280x Cheaper. Your Bill Didn’t.
A client asked me whether he should delay his AI project another quarter and let model prices fall further. Wrong question. Per-token pricing has fallen as much as 280-fold since 2022, and enterprise AI budgets…
The App Store for AI Just Opened. Your Infrastructure Isn’t Ready for It.
For two years the AI market was a bake-off over whose app was smarter. A quiet standard called MCP just changed the question entirely from “which AI app should I buy?” to “can my business…
Your AI Vendor Is Hoping You Don’t Ask About Security
I’ve sat in a lot of vendor demos. The slides are beautiful, the demo runs flawlessly, and nobody says a word about where your data goes or who can read it. That silence isn’t an…
Your AI Pilot Worked. That’s Exactly Why It’ll Fail in Production.
The most dangerous sentence in AI right now is “the pilot was a success.” A failed pilot tells you the truth while the check is small. A successful one tells you a flattering lie—that the…
Uber Burned Its Entire 2026 AI Budget in Four Months. The Real Lesson Isn’t About Money.
In April, Uber admitted it spent its full 2026 AI budget in four months — and its own COO couldn’t connect the spend to customer value. The easy read is “AI is expensive.” That read…
What AI-Ready Infrastructure Actually Costs to Build
A client wanted one number for getting “AI-ready” before our call ended. Three vendors had already given him one — and that’s exactly the problem. The number you’re quoted is almost always the model, the…