In episode 46 of Generationship, Rachel Chalmers and Don Marti trace a thoughtful arc from the open source protests of the 1990s to today’s AI-driven world. They explore how large language models blur truth and plausibility, debate ethics in benchmarking and market-based definitions of intelligence, and mourn the loss of the web’s early democratizing promise. Don discusses sustainable open source ecosystems, AI tooling, and practical advice for new graduates navigating an AI-saturated job market.