At 12:04 on August 23, 2026, something quietly rewrote my outreach DM schedule down to three runs a day — 2:31 AM, 10:31 AM, and 6:31 PM. For the several days it took me to notice, that cost me dozens of missed opportunities every single day. I still don't know what did it.
Why this mechanism works
The problem: you can't tell when automation has stopped
When you strip away the details, making money as a solo developer comes down to one equation: automation uptime = revenue. I was a college student making 100k yen a month, then 600k a month juggling multiple gigs, then back to zero when I was laid off for company reasons — and the reason I could build a Claude Code autonomous environment in six months and get to 1.2M yen in monthly revenue is that I had an outreach DM lane running while I slept.
Automated outreach DMs are made up of four launchd jobs. Instagram, Threads, follower prospecting, and YouTube each have their own independent plist and Python script. These control their start times via StartCalendarInterval. For example, com.lily.outreach-ig runs eight times at 8:20, 10:20, 12:20, 14:20, 16:20, 18:20, 20:20, and 22:20, and com.lily.outreach-th runs seven times every two hours from 9:38 to 21:38 — sends happen during daytime hours.
