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How I Built a Personal LifeOS with AI

TL;DR Your life generates too much information to organize by hand. Mine does too. I built a three-layer system: raw documents (Google Drive), a living wiki (Notion), and an AI agent that maintains both. The agent isn't smart. The system is predictable. That's why it works. This post covers the architecture, the schema, and the file tree. I'm a product counsel by day. Outside of work, I'm an IVF patient tracking insurance, appointments, and claims; an investor managing accoun

2 days ago8 min read

Chat with Stephen Elkind, Product Counsel @ Google

A candid conversation with a Google attorney counseling the teams for Gmail, Google Meet, and Gemini in Workspace. Stephen chats about...

Sep 14, 20255 min read

Chat with Tilak Koilvaram, Lead Product Counsel @ Plaid

“Product counsel[ing] isn’t rocket science.” But “be a nerd about the business.” Tilak’s path (snapshot) Law firm: Davis Polk (IP & Tech...

Aug 17, 20254 min read

Breaking in-house (Post 2)

What if I make the wrong move? My first jump in-house — though to a respectable and successful company — was not a fit. I soon realized...

Aug 11, 20252 min read

ABOUT ME

Sharing my process to becoming a successful General Counsel.

Inspired by Austin Kleon's Show Your Work!

Resume

Lead Product Counsel @ Ramp.

Previously:

Policy Counsel @ Paradigm
Associate @ Debevoise
Student @ Harvard Law School
Project Coordinator @ Berkman Klein Center for Internet and Society

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Recent Fave

This show absolutely toppled me.

What are the consequences of every human given the option to leave our physical bodies, and upload our minds to a cloud? No more disease, no more hunger, no more pain. But what happens to our families? Our love lives? What about society? What about geopolitics?!

Throughout, you're wondering how this show could possibly raise the stakes in the next episode. But by the end, your reconsidering your own philosophy of life.

I adore dystopian tech stories, and this mashed together all my loves: the glorious animated art of Love, Death & Robots, the storytelling of Ken Liu, and the heart-wrenching character development of The Matrix. As you watch, you think the show might offer the viewer a chance to breathe. But no. It's a turbo-charged pace from frame one.

It'll be a while until I watch something this good again...

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