We Automated Everything With AI and Tripled Our Headcount

Dan Shipper runs one of the most AI-native companies today. Every has agents embedded in nearly every workflow—“if you swing a stick in our Slack, you're as likely to hit a human as an agent,” he says. And yet the company has grown from four people to 30 since GPT-3 came out, and is still hiring. Why does Dan believe there's more human work to do than ever? In a format flip for AI & I, Every's COO Brandon Gell turns the tables and interviews Dan about his latest essay, “After Automation”—an 8,000-word argument for why rising automation doesn't eliminate demand for human work, it increases it. The thesis: AI makes yesterday's expert competence cheap and widely available, which floods every field with output that's close but not quite right—and that creates more demand for the humans who can take it the rest of the way. Dan talked with Brandon about the paradox at the heart of agent-native work: The more AI can do, the more humans are needed to direct it, refine its output, and decide what matters next. If you found this episode interesting, please like, subscribe, comment, and share! To hear more from Dan Shipper: Subscribe to Every: https://every.to/subscribe Follow him on X: https://twitter.com/danshipper Links to resources mentioned in the episode: “After Automation” by Dan Shipper: https://every.to/chain-of-thought/after-automation Brandon Gell on Every: https://every.to/@brandon_5263 Join the membership for where you live at ⁠joinbilt.com/dan⁠ Timestamps: 00:00:51 Introduction 00:05:51 The AI paradox: more automation, more human work

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Uploaded Jun 12, 2026

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