When a Massachusetts landlord discovered his tenants were using free legal aid and AI to exploit every loophole in the book, he stopped losing sleep and started building a weapon of his own. In this episode, Goodstander founder Caleb Wursten breaks down how he went from redeveloping Rust Belt towns like North Adams to creating a "landlord operating system" that scans your messages for legal risk before you hit send. From the brutal realities of eviction, security deposit traps, and hostile tenant laws to the ethics of AI giving legal guidance, this conversation is a must-watch for anyone who owns property in a tenant-friendly state.