Personal Project

Your
Second Brain

A personal knowledge system that lives in your iCloud Drive and remembers everything you don't want to lose track of, so you don't have to.

RoleCreator & Vibe Coder
Year2026
TypeAI / Personal Tool
🧑‍🤝‍🧑
Frontal — People
Friend A · birthday Jul 12 · obsessed with Blue Bottle
Friend B · met at Recurse · follow up re: residency
47 contacts tracked →
🎯
Frontal — Goals
Ship Second Brain v2 · by end of Q3
Run a sub-1:50 half · Berlin, Sep 27
9 active goals →
💡
Parietal — Ideas
Markdown beats databases · outlives every app
Retrieval > storage · captured Mar 14
132 notes captured →
📚
Parietal — Learning
Rust ownership model · halfway through the book
Espresso pulling · dial in 18g → 36g in 28s
6 topics in progress →
📍
Occipital — Places
Tartine, SF · morning bun, weekend mornings only
Onsen Spa · book 3 weeks out, ask for the back room
28 places saved →
📅
Occipital — Events
Sister's birthday dinner · Jul 12 · book State Bird
Investor sync · Apr 30 · prep retention deck
14 upcoming →
HOVER A LOBE TO EXPLORE
Overview

You forget things.
This doesn't.

~/iCloud/SecondBrain · brain query
$ brain "what does my sister care about right now?"
 
→ reading people/sister.md, events/, inbox.md…
→ cross-referencing 14 mentions across 6 files
→ generating answer…
 
✓ done in 340ms · see response ↓
 
$
01
It lives where you live
Plain Markdown files in your iCloud Drive. No app to install, no account to make, no vendor to outlast.
02
You write like you talk
"brain add, sister loves pottery now." The model picks the file, the folder, the format. You never decide where things go.
03
Answers, not search results
Ask anything. The brain reads across files and writes you back in plain language, like a friend who was paying attention.
B
Brain · answered in 340ms · 6 files referenced

Your sister's pretty deep in pottery right now. She signed up for a wheel-throwing class in February and you noted she's been venting about glaze chemistry. She's also training for a half-marathon in September, which is why she's been quieter on weekends.

Reading-wise, she's working through Murakami again (you lent her Norwegian Wood last fall and she still has it). On the food side, she'll eat almost anything except cilantro, and the owl thing from your dad's birthday is still a sore spot, so steer clear.

One thing worth following up on: she asked about your move on Mar 14 and you never circled back. Her birthday is Jul 12. Last year you forgot until the day-of, so you flagged this one to remind you a week early.

Sources people/sister.md events/2026-q3.md preferences/food.md inbox.md links.md + 1 more
"The real power isn't storage.
It's retrieval."
The Problem

Human memory fails
in predictable ways.

Not randomly. Always the same categories. Always the same moments.

💬
Context scatters across tools
A birthday in iMessage. A restaurant in Notes. An idea in a voice memo. A thesis in a screenshot. None of it connects. All of it gets lost.
🔁
We solve the same problems twice
Past context disappears. You read the same article twice, make the same mistake, forget the same lesson. Memory without structure is just entropy.
📋
Existing systems require too much discipline
Obsidian. Notion. Apple Notes. Milanote. Notability. Gmail. They all require elaborate tagging and consistent habits. Most people quit within weeks. The friction is the product killer.
🎂
People matter. We treat them like tabs.
You forget your friend's birthday. You don't remember what your roommate told you last month. You show up to a conversation without context. That's not who you want to be.
My Approach

Design for zero friction.

The moment capturing something feels like work, people stop. Every design decision pushed toward: make it as easy as talking.

01
Start with where information actually lives
Not a new app. Not a new habit. iCloud Drive: already on every device, already syncing, already trusted. The brain lives where your life already lives.
Infrastructure
02
Let AI do the routing, not the user
You say "brain add this." The AI decides where it goes: people/, events/, preferences/, links.md, or inbox.md. No tags. No folders. No decisions.
AI Routing
03
Build a living index at the top
_index.md stays continuously updated, a readable map of everything the brain knows. At a glance you can see the whole system. Legibility is a feature.
Information Architecture
04
Optimize for retrieval, not storage
Structure every entry so it can be found by a natural language question. "What did my advisor say about semis?" should work. Storage without retrieval is just hoarding.
Retrieval Design
Under the Hood

How it actually works.

Plain files. Smart routing. No database. No backend. Just Markdown and a brain that knows where things belong.

~/iCloud/SecondBrain 42 files · 2.1 MB
SecondBrain
_index.md
people/
sister.md
advisor.md
events/
inbox.md
Folder Architecture
Every file is Markdown. Every folder is a category. The AI routes; the files store. Nothing proprietary. It's your data, in your iCloud, forever.
~/iCloud/SecondBrain/
├─ _index.md  # always up to date
├─ people/
  └─ sister.md, advisor.md…
├─ events/
├─ preferences/
├─ links.md
└─ inbox.md
routing.ai ~12ms
$ brain add "sister loves jazz bars"
CLASSIFY
people/sister.md
events/
preferences/
inbox.md
The Routing Brain
When you say "brain add this," an AI layer reads the content, classifies it, and appends it to the right file with the right structure. It learns your patterns.
# Example input
"brain add, sister loves jazz bars"

# Routes to: people/sister.md
## Interests
- Jazz bars · mentioned Mar 2025
Why Markdown over a database
Markdown files are human-readable, portable, version-controllable, and will outlive every app ever built. A database is a product. Markdown is a format. The goal was to build something that compounds over years, not something that breaks when a startup pivots. Your Second Brain should still work in 2040.

Want to build your own?

This is a personal project, but the concept is open. If you're curious about the setup or want to talk about it, reach out.

Ben Gleeman

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