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I Shouldn’t Have to Tell the Intelligence

Michael and Damashe explore what happens when AI tools are asked to work instead of simply answer questions. Damashe shares his experiences using ChatGPT to reorganize a Numbers spreadsheet, Claude to manage email, and an AI-assisted product search that produced a very convincing but completely inaccurate hard drive price.

That leads to a larger question: If you ask AI to research something, should you also have to tell it to search the web and verify the information? They discuss the rough edges of today’s AI agents, why this period feels like the early days of personal computing, and whether these tools will eventually become reliable enough to work without constant supervision.

They also talk about software companies rewarding new customers instead of loyal ones, VoiceOver and Zoom frustrations, sharing health data with AI, configuring ChatGPT and Codex on the Mac, repurposing computers as servers, and the photo they forgot to take when they finally met in person.

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