The Bothness of It — with Alex Hillman

Alex Hillman built one of America's first co-working spaces, wrote a business book in tweets, and recently handed his inbox to a Claude Code agent — not to draft emails, but to notice when a friendship is going cold. In this episode, Alex, Michael, Wes, and Hadley dig into marketing for people who hate marketing, what 20 years of email reveals about your relationships, and why the hardest part of AI-assisted coding was always the part before you wrote a single line. Alex Hillman is co-founder of Indy Hall (one of the first co-working spaces in the world), co-founder of Stacking the Bricks, and author of “The Tiny MBA.” He lives and works in Philadelphia, where he thinks seriously about community, trust, and karaoke song selection. What's Inside: • Marketing is really just listening at scale • Building a 20-year relationship database from your sent folder • "Hot rod vs. plumbing" — the two kinds of software you build now • What early internet and the AI boom have in common • The case for reading 20-year-old engineering books with a coding agent • Karaoke philosophy as a framework for community building