Second Shift Club

“Second shift” means two things here.

The first: the systems. Agents and automations that keep working after you log off. Small teams have never had access to leverage like this before. Most of them don’t know where to start.

The second: what it takes to learn all this. If you’re figuring out AI tooling after hours — evenings poking at prompts, weekends reading docs, trying to turn “we should be doing something with AI” into something that actually runs — that’s a second shift too. Nobody assigned it to you. You took it because you could see where things are going.

This newsletter is for people working that shift.

Every issue is one practical guide: a real system, written up so you can build it yourself. The actual steps, the tools, what it costs, where it breaks, and a template to steal at the end. No frameworks invented for the post. No “invest more in brand.” If you’ve ever been handed a goal like “get us mentioned in LLMs” and then had to go produce something — this is the operations manual I wish someone had handed me.

Written by Drew Wilkinson. I work on a lean AI search and systems team at Sinch. I learned everything here the same way you’re learning it: on the second shift.

The goal, eventually, is that the first meaning replaces the second. The systems work the nights so you don’t have to. ;)