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Welcome, AI Strategists

💫 Current thoughts: A senior marketer on my monthly Roundtable said something that's been sitting with me: "I feel ignorant on AI."

He's not. He's smart, experienced, technically competent. He just can't use AI in any meaningful way at work. His IT team has restricted him to a single sanctioned tool that can't do real work. Meanwhile, on the same call, his peer demoed an SDR forecasting app built in four hours. Same kind of role. Same kind of person. Different worlds.

This week's post is for the practitioners stuck on the wrong side of an IT-policy lockdown, and for the leaders who set the policy without seeing what it's costing them:

  • Why "responsible governance" has a vendor underneath it (Microsoft has spent a year positioning governance as their selling point)

  • The cost of compliance that nobody is measuring, with the academic data that names it

  • Three moves to make before you accept the lockdown, plus what it tells you if none of them work

If you're locked out, the post gives you three specific moves to try this week. If you're the one who set the policy, it names what the current policy is costing the business.

This Week's Breakdown

AI News Roundup for SMB Decision-Makers and Marketing Professional

Talk to your AI tools the way you'd talk to a colleague.

You don't send a colleague a three-word brief. You explain the context, the constraints, what you've already tried. But typing all that into ChatGPT takes forever — so you don't.

Wispr Flow lets you speak your prompts instead. Talk through your thinking naturally and get clean, paste-ready text. No filler words. No cleanup. Just detailed prompts that actually get you useful answers on the first try.

Millions of users worldwide. Works system-wide on Mac, Windows, and iPhone.

  • 🪑 The trial of the century, now with lumbar support.

  • 🤖 "AI Marketing Orchestrator" is just "the person who untangles the mess we made automating everything."

  • 📦 Amazon now delivers faster than you can find your phone to cancel the order.

  • 🤔 Teaching AI to distrust itself turns out to be the best prompt engineering advice nobody gave you.

  • 🖥️ Sixty-one percent of US workplaces now use AI to monitor productivity, which is a lot of software doing a lot of judging from people who've never done the job.

  • 🗂️ Microsoft researchers discover AI corrupts documents 25% of the time, which is apparently the acceptable loss rate for "productivity."

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