Cup Club is a coffee, tea and milk subscription I started for the IT:U cohort in February 2026. Members pay a flat monthly amount and take as much as they want; the club buys in bulk and keeps an open ledger that any member can ask to see.

There are three tiers: Heavy (€10), Casual (€5) and Paused (€0). The Paused tier is the part that was designed rather than inherited. A member who stops drinking coffee for a month sets their tier to zero and stays on the roster, instead of leaving and having to rejoin. It costs the club nothing and removes the one thing that would otherwise shrink it: the awkwardness of quitting. Nineteen people are on the roster, and between eight and seventeen were active each month from February to June 2026.

Most of the day-to-day running, from the money to keeping track of members, is handled by an AI agent I set up.