Up until a few years ago, Cole Rubin managed a $19 million residential portfolio of around 200 properties across Airbnb and Booking.com. He lived the midnight guest messages, the missed calls, the inbox chaos. That firsthand pain led him to build Conduit, an AI agent platform for hospitality. Guest requesting a late checkout? An agent checks availability, takes payment and updates the cleaning team, all without a human in the loop. Cole joins Matt to talk late checkouts, AI agents and the future of hotel guest communication.