A Facebook Messenger bot for pilots, built during the 2016 chatbot wave. Thousands of pilots around the world used it to get METARs, TAFs, NOTAMs, animated radar, wind-favored runways, and even airport restaurant recommendations. The big design challenge was making a conversational interface feel fluid and natural years before LLMs existed. Everything was built with NLP and state machines. Creating it taught me that people don’t actually want pure conversation with a computer, they want the right information surfaced with the least friction. That insight shaped a lot of how I think about interfaces today.