Over the weekend a friend told me about how he set up his AI OS. I've been loosely working on something similar myself, so I paid attention.
He sent me this video. It's 20 minutes long. Rather than watch the whole thing, I loaded it into Cowork — it came from a trusted friend, I don't need the full walkthrough. I need the gist, because I need to start experimenting with the setup.
The biggest problem I've had lately is losing context between sessions. It's really annoying. That's the main issue I'm trying to solve right now. I'm working alone, figuring this out on the fly.
Let me preface this by qualifying that I am not that technical. On a scale from boomer noob to 10x developer, I'm probably a 5 or 6. Technical enough to figure things out on my own, but I don't have 20 years of programming behind me. The 20 years I've had in the software world are as an entrepreneur. I think in business terms, not developer terms. A real 10x dev — and I've met maybe 2 or 3 in 20 years of hunting in the space — would come and laugh at my naivety.
I'm not going to say I've fixed this issue. But Obsidian seems to be heading in the right direction. Rather than claim it works, I'll say this is what I'm checking out right now and it looks promising. Here's what I did. If you're having this problem, you can try it out. I'll report back in a few days or a week or two if I'm loving it.
The Problem
Every Cowork session starts blank. Corrections, decisions, and project context die when the session ends. Even facts you've corrected five times get forgotten. I told Claude I was out of my previous company — multiple times, across multiple sessions. Every new session, it forgot.
The Fix
Use your Obsidian vault as the same folder you mount in Cowork. One folder, two tools looking at it. Claude reads three files at session start: a dashboard snapshot, the last session's handoff notes, and a corrections log. At session end, Claude writes a handoff file so the next session knows exactly where to pick up.
Session memory lives in markdown files on your computer. Not in Claude's head.
Here's the structure I built:
- Numbered folders (00-Dashboard through 05-Session-Handoffs) form the memory layer
- A Corrections Log catches mid-session fact changes in real time so they actually persist
- A handoff file written at session end tells the next session exactly where to pick up
- Working files (images, HTML, scripts) go in
_working/to keep the vault clean
The Timeline
I started setting this up at 8am. Finished the vault structure, cleaned up my file system, organized 42 working files, fixed a stale system prompt that had been feeding Claude wrong info for weeks, and wrote this post — plus a few other tasks running in the background. Done by 9:28. 90 minutes.
The Numbers
Revenues: 0 Clients: 0 Prospects: 1, with another 2 possibles in the pipe