Latest — 26 Jun 2026 Episode 71 - Ask Better Questions Educate yourself enough to "kinda get it," then ask good questions, then judge the output.
Episode 70 - AI or Not? AI-generated and AI-altered images have gotten genuinely, unsettlingly good. That's wildly useful and also dangerous!
Episode 69 - Wait, what's the difference between a Skill and a Project? A Skill is a repeatable task. A Project is reference material. Cowork is a Project that can use your computer. They aren't competing products; they are different places to put your context.
Episode 68 - Don’t Blame the Robot Most “AI-driven layoffs” aren’t actually driven by AI. The technology is used as a cover for cuts that were already coming for different reasons. No one wants to admit the real reason, so it is easier to blame the robot.
Episode 67 - It’s not your prompts Use AI for thinking (not deciding), fix the system (not the output), and correct without drama.
Episode 66 - Don’t Tell Claude Who to Be Tell it what task it's doing and what scope it's working in. The "you are an expert" prompt is mostly cargo cult now; a list of NEVER statements is brittle.
Episode 65 - How to tend a codebase I double down on the idea that keeping up with AI-generated code looks a lot like gardening: seeds, soil, water, pruning, weeding, and sometimes pulling up a plant.
Episode 64 - Context is King The number one reason folks struggle with AI tools is they don't give the model enough to work with. Context is the cheapest upgrade you can make to any AI workflow today.
Episode 63 - AI in ArcGIS, How to Start Esri now has a whole family of AI assistants built into ArcGIS—Arcade, Pro, Survey123, Item Details, Story Maps, Hub, Documentation, and more. I suggest starting with a workflow you do every week so you can start to learn when to trust the AI tools.
Episode 62 - Break The AI I built an 8-bit video game-style AI red teaming game that lets you try to break various chatbots with different guardrails so you can see how it works.