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Every week, I write a deep dive into some aspect of AI, startups, and teams. Tech exec data storyteller, former CEO @Textio.
Tin can in the sky A few years ago, I was flying across the country for a business trip and counting on the flight to get some work done. Unfortunately, the wifi was out for the entire trip. When I landed, I complained about it to a coworker. "Yeah, that's annoying," he said. "On the other hand, you just spent a few hours inside a tin can in the sky, and now you're 3,000 miles away from where you had breakfast this morning. Technology is amazing!" Take two things from this story. One, it is...
The prompt industrial complex These days, AI can produce most common workplace artifacts. From emails to slide decks to financial models to working code, a workable first draft is often just one prompt away. Ok, maybe not one prompt away. It usually takes a few tries to describe exactly what you want. If you care about quality, getting a credible artifact typically involves several prompt <> production cycles. AI refines its output based on how you evolve your prompt, and you refine your...
Prognostication vs. reality I spent 2025 as Founder in Residence at Operator Collective, a venture firm whose LPs include many of the most successful tech leaders of the last decade. During that year, I spent time not only with hundreds of AI startups but also with these operators. For me, these discussions informed several predictions about AI that are now coming true, So I was extra interested in the data set that Operator Collective dropped last week. They surveyed the operators in tech...