When we started this podcast, AI was a quirky sidekick—good for autocomplete, bad at facts, and mostly harmless. Fast-forward three years and suddenly it’s writing code, composing music, summarizing our thoughts before we finish them, and politely asking whether it should schedule the meeting instead. In this episode, we look back at how ChatGPT and other AI tools evolved alongside our podcast—from novelty demos and broken prompts to always-on copilots and mildly unsettling digital coworkers. We talk about what genuinely improved, what’s still gloriously flawed, and how our expectations quietly shifted from “this is fun” to “wait, this actually works.” A nostalgic, slightly sarcastic progress report on watching AI grow up—while our microphones, workflows, and existential questions remained suspiciously unchanged.