jobaicantdo

The Job AI Can’t Do

The Job AI Can’t Do Block let almost 4,000 people go in February. That’s not a typo. They went from roughly 10,000 employees to under 6,000 in a single cut, and Jack Dorsey said the reason was AI. Atlassian cut 10% of its global workforce a few weeks later, citing the “AI era.” Baker McKenzie, the law […]

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INBOX INSIGHTS: What Does AI Cost You, Vibe Coding Part 2 (2026-08-12)

INBOX INSIGHTS: What Does AI Cost You, Vibe Coding Part 2 (2026-08-12) :: View in browser 👉 Read our newest paper on what jobs AI can actually take! Watch This Newsletter 🎧 Listen to this newsletter as an MP3 What does AI cost you? I saw a post on Threads last week, and I haven’t […]

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entaipt1

Enterprise AI Part 1

In this week’s Data Diaries, we kick off a seven-part series on enterprise AI with the question every CFO eventually asks: how do you actually know what this stuff is worth? Start with TRIPS — Trust Insights’ five-factor screen for whether a task even belongs near an AI system. Take any task on your desk and […]

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90dayaiplans

Realistic 90 Day AI Plans

A Realistic 90-Day AI Plan This is the last issue in the series. Thank you for sticking with me through the last three pieces. You’ve learned more about the unglamorous side of AI work than most in our field are willing to share. That matters. Quick recap of where we’ve been: Issue 1: The gap isn’t […]

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ai command line tools

AI Command Line Tools Part 1

In this week’s Data Diaries, let’s walk through a few of my favorite command line tools in a new series, something that we’ve discussed recently on the podcast and livestream. As a refresher, command line tools are terminal-based pieces of software that typically do specific functions or tasks. Every computer has a command line or terminal. […]

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aistrategygaps

AI Strategy Gaps

The Strategy You Already Have Isn’t the Problem I want to share something I’ve been hearing on almost every client call for the last six months. It comes in different words, but it’s always the same conversation. Their AI strategy gaps. “We’ve been to the workshops. We had the leadership offsite. We hired a consultant […]

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Productizing Expertise

Your Expertise Is Already a Product. You Just Haven’t Packaged It Yet. Here’s the thing. If you run a consultancy, an agency, or really any knowledge-based business, you have been building products for years. You just didn’t package them as products. You packaged them as “deliverables” inside a consulting engagement and moved on to the […]

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aidigitalclone

AI Digital Clone Part 4

In this week’s Data Dairies, we move onto the fourth and final part of the AI digital clone series. Last time, we obtained the final output of my thinking catalog, the top 20 ways I solve problems. That’s useful and helpful by itself, but now we need to make it useful and operational. Remember that […]

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b2mmarketing

Business To Machine (B2M) Marketing

The Most Important Audience You’re Completely Ignoring About seven years ago, Chris and I sat down and tried to work through an idea that was bugging us. We’d been thinking about audience segmentation — B2B, B2C, the usual suspects — and we kept coming back to this thing that didn’t have a name yet. There […]

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How To Manage Overwhelming Productivity

How To Manage Overwhelming Productivity

When You’re So Productive You Forget What You Did I’m going to tell you something that happened to me this morning, and I need you to not judge me. (Or judge me. That’s fine too). I officially experienced overwhelming productivity. We had our team call today, and one of the things on the agenda was […]

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