I spent the better part of today building something I’ve been thinking about for a while: a proper second brain.
Not the kind where you dump notes and forget them. The kind where your meetings, your thinking, your strategy, and your client work are all connected — where a note from today’s client call links back to the SWOT you wrote last month, which links to the entity pages for your key people and companies.
Here’s what we built and why I think every CEO running multiple companies should do the same.
The problem with how most CEOs take notes
Most notes are dead ends. You write something down, file it somewhere, and never see it again. Your past thinking doesn’t inform your current decisions. You can’t search for “everything I’ve ever discussed about AEO” and get a coherent picture.
I’ve been recording all my meetings with Plaud for months now. But the raw transcripts are almost unusable — 40,000 characters of Taglish mixed with crosstalk and background noise. Plaud’s AI summarizes them, but the summaries sit in a Slack channel and go nowhere.
Today we changed that.
The architecture
Every Plaud recording now automatically flows into my Obsidian vault as a structured CEO-format note. And I’m not talking about a transcript dump — this is an actual synthesized note with:
– Executive summary (3-5 sentences of what actually happened)
– Decisions made
– Action items with owners and deadlines
– My personal commitments
– Issues and risks flagged
– Topic-by-topic breakdown
But the more important part is what happens after the note is created. Every entity in the note — a client company, a team member, a concept like AEO or Share of Voice, a project like Business Beyond Limits or Rankseer — gets automatically linked using Obsidian’s wikilink system.
So when I open a specific meeting note, I can click through to the every entity included in that meeting, which shows every meeting we’ve ever had about them. I can click through to the AEO concept page, which shows every context where I’ve discussed it — client pitches, internal strategy sessions, all-hands meetings.
The graph view in Obsidian turns this into a visual knowledge map. You can see which clients are most actively discussed, which concepts are most central to your business, which people appear across the most contexts.
The technical setup
The vault lives in the cloud, synced across my desktop and phone via a self-hosted CouchDB instance running on a cloud server. Obsidian’s LiveSync plugin handles the real-time sync between devices.
Every Tuesday morning, the system pulls from that week’s meeting notes plus my any other notes that i include – and generates strategic plans, ideas and write-ups for me and my team to review, learn from and gather business insights with.
The whole thing runs on OpenClaw – with my AI agents handling the orchestration. When a new Plaud summary lands in Slack, it gets processed, formatted, linked, and written to the cloud within 15 minutes.
Why this matters for CEOs
The point isn’t the technology. The point is that your thinking compounds when it’s connected.
Right now I can open any meeting note and trace the thread back: this client discussion connects to this strategy session connects to this hiring decision connects to this SWOT analysis. The context that usually lives only in my head — or gets lost when I’m busy — is now retrievable.
I wrote about how listening and context affect decision-making a while back. The second brain is the infrastructure that makes that kind of contextual decision-making possible at scale.
You spend eight to ten hours a day generating insights, decisions, and commitments. Most of that disappears by the end of the week. A system like this turns that daily work into compounding organizational intelligence.
What’s next
I’m progressively adding historical recordings. We’ve processed about only 16 meetings so far. There are probably 50 more worth adding from the past few months. Each one adds another layer of connected context.
If you’re running multiple companies and your institutional knowledge lives mostly in your head and in scattered Slack threads, this is worth building. The setup took most of a day. However, the compounding value starts immediately.
