THE AI BUSINESS PLAYBOOK • Issue: #27 • Read time: 4 min ♟️ The Leverage Point You can now draft the status update, summarize the meeting, and turn rough notes into a plan faster than you could a year ago. That's useful. It's also how unclear work becomes polished waste. The question before using AI isn't always “How can I do this faster?” Sometimes it's “Why are we doing this at all?” Keep reading. Estimated read time: 4 minutes A request lands in your inbox. “Can you pull together a quick...
4 months ago • 4 min read
THE AI BUSINESS PLAYBOOK • Issue: #26 • Read time: 4 min ♟️ The Paradox The "best" AI model is often the most expensive way to do the easiest task on your list. A team I've advised hit their usage cap three days into the month and spent the rest of it locked out of frontier models entirely. A team I've advised burned through their entire month's AI budget in three days. live view of my reaction first hearing this Not because they were doing anything impressive with it. Not because they'd...
4 months ago • 3 min read
THE AI BUSINESS PLAYBOOK • Issue: #25 • Read time: 4 min ♟️ The Paradox: The most advanced agentic engineering workflow publicly documented was built by an L8 principal engineer with 20+ years at Meta, Microsoft, and Atlassian. I'm a Technical Program Manager. No CS background. Never touched a terminal in my life. Last week I got the same stack running. Not a simplified version. Not a no-code shortcut. The actual stack. Here is what week one looked like for someone starting from zero. I am...
4 months ago • 4 min read
THE AI BUSINESS PLAYBOOK • Issue: #24 • Read time: 4 min ♟️ The Paradox: The more you know, the harder it is to let AI help you. Most professionals assume they will get better at AI as they gain experience. But expertise is not neutral. The more confident you are in what you already know, the more likely you are to use AI to confirm your thinking rather than challenge it. You have probably watched this play out in a different context. The family member who has "seen everything" and cannot be...
4 months ago • 3 min read
THE AI BUSINESS PLAYBOOK • Issue: #23 • Read time: 4 min ♟️ The Leverage Point The professionals pulling ahead with AI aren't the ones with the most tools. They're the ones with the most readable context. Almost nobody is building it. Here's the 3-layer system that actually compounds. Let me show you two versions of the same Tuesday morning. Version A: You need to prep a business review for your VP:First, you open an AI tool. Then type: "Help me write a business review." Which gives you a...
5 months ago • 5 min read
THE AI BUSINESS PLAYBOOK • Issue: #22 • Read time: 4.1 min ♟️ The Leverage Point Most professionals see the layoff headlines and ask the wrong question. They ask: "Is my job safe?" The operators pulling ahead are asking something different: "Am I building workflows, or am I just sending prompts?" Those are not the same job. One of them disappears. One of them gets pulled into more rooms. Here is what four layoffs this week made clear, and the one shift that changes your answer. Keep reading....
5 months ago • 5 min read
THE AI BUSINESS PLAYBOOK • Issue: #21 • Read time: 4 min ♟️ The Leverage Point Most professionals try to automate everything at once and end up with nothing running. The operators pulling ahead built one workflow, and built it backward from the output. Here is the exact process. A few weeks ago, my company let go of an entire engineering team. Not because the work stopped. Because the math changed. (don't worry, we were able to offer them other roles inside the company or gave them the option...
5 months ago • 3 min read
THE AI BUSINESS PLAYBOOK • Issue: #20 • Read time: 4 min ♟️ The Leverage Point One founder. Zero employees. $30M raised. AI ran the fundraise. He showed up for signatures. Same week: ClickUp announced it's laying off to rebuild around 100x players with million-dollar salary bands. Meta cut 8,000 and posted external engineering roles the same day. None of this is unrelated. All of it is pointing at the same shift. The second law of thermodynamics says that in any closed system, disorder...
5 months ago • 3 min read
THE AI BUSINESS PLAYBOOK • Issue: #19 • Read time: 4 min ♟️ The Leverage Point A team recently got an internal memo about AI usage. It said frontier models cost 10 to 50x more than standard ones. Use them "only when necessary." Nobody defined what necessary means. That gap (between the rule and the framework) is costing teams real money every month. And it's not unique to that team. Here's what the memo should have said instead. Keep reading, and you'll have something you can use before your...
6 months ago • 3 min read