Eleven days out from the next event. Instead of mass-blasting the roster, I segmented attendees into four tiers — Hardcore, Casual, Lost Regulars, One-Timers — and wrote a different message for each. AI drafted the templates. I approve each send. Slower than letting it rip but it’s my name on the text.
The annoying part is still manual: cross-referencing Venmo handles against Facebook profiles against my phone’s contacts. Each person has 1–3 contactable channels and only one of them actually gets read. No good answer yet.