Connecting Claude to the cloud folder

What if the cognitive overhead of constant context-switching, endless meetings, and deciding what to work on next could be offloaded to a system that actually knows how you think?

In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Michael Leibovich, a business unit leader at Adobe overseeing product, design, support, and business strategy, who spent his paternity leave building something most people only talk about: a fully personalized AI chief of staff, built on Claude Code, powered by nothing more than folders and markdown files.

They explore the architecture behind Michael’s system in detail, from session memory and mental models to a people file that auto-updates from meeting transcripts, a knowledge graph that grows over time, and scheduled tasks for daily meeting metabolization and weekly competitive intel. Michael walks through how he bootstrapped his minimum viable context by extracting from ChatGPT’s memory in under ten minutes, why Obsidian became his visual interface of choice, and the moment he realized this was genuinely worth the investment: getting a suggested answer to “what is the highest leverage thing I should do right now?” in a 30-minute gap between meetings.

If you’re a non-technical operator overwhelmed by AI tooling and unsure where to start, a leader constantly context-switching between teams who struggles to protect time for deep work, or someone building out your own context infrastructure and looking for a real-world playbook, this episode is for you.

All episodes of the podcast are also available on Spotify, Apple and YouTube.

New to the pod? Subscribe below to get the next episode in your inbox 👇

Want company-specific interview intel?

If you’re preparing for PM interviews at Anthropic, OpenAI, Google, Stripe, DoorDash, Uber, or Figma… we think you’re going to love Insider Loops. You can read about it in Ben’s LI post, Marc’s LI post or check out the site directly below.

In this episode, we covered the following topics:

* (00:02:08) Why Michael built this: context overload, starting over every time, and the desire for an AI that actually knows him

* (00:13:44) The architecture: just folders and markdown files, no code required

* (00:15:00) The four layers: personal wiki, mental models, voice calibration, and operating protocol

* (00:17:47) Claude Code in the desktop app vs. terminal — and why the app removes the biggest barrier to entry

* (00:21:32) Local storage vs. GitHub: backup anxiety, security tradeoffs, and why GitHub unlocks cloud-based scheduled tasks

* (00:22:37) Earmark for real-time meeting transcription and how it feeds the system

* (00:27:45) Minimum viable context: extracting three pages of foundational context from ChatGPT memory in ten minutes

* (00:30:00) The aha moment: “What is the highest leverage thing I should do in the next 30 minutes?”

* (00:33:50) Obsidian as the visual interface for the Claude folder system

* (00:37:10) The knowledge graph: beliefs, decisions, and a people file that auto-updates from meeting notes

* (00:49:00) Calendar ingestion and the one-pager Michael wishes everyone brought to meetings

* (00:56:01) Where to find Michael and how the audience can be helpful

* (00:57:08) Gratitude Corner: Thanking ex-bosses (Amanda, Wendy, Zoe, Beth), his wife and a dear friend, Will

* And more!

Links:

* Michael Leibovich’s Startup Dad episode:

https://startupdadpod.substack.com/p/create-your-parent-advisory-board-michael-leibovich-adobe

* Earmark (notetaking tool for PMs): https://www.tryearmark.com/

* Obsidian: https://obsidian.md/

* Helpful resources to get started with Claude Code and Obsidian:

* Claude Cowork: The Definitive Setup Guide (works for Code interchangeably): https://x.com/witcheer/status/2027759832523051263

* Claude + Obsidian: The Memory Stack: https://x.cosssm/nyk_builderz/status/2030904887186514336

* CC Chief of Staff Setup Guide (github link): https://github.com/jimprosser/claude-code-cos

* Zoe Black: https://www.linkedin.com/in/zoeblack1/

* Wendy Baker: https://www.linkedin.com/in/wendymbaker/

* Amanda Patterson: https://www.linkedin.com/in/amandawpatterson/

* Marc: https://www.linkedin.com/in/marcbaselga/

* Ben: https://www.linkedin.com/in/benerez/

If you’re a new subscriber, we encourage you to check out some of the recent episodes you might have missed:

To support the podcast, please check out the links below:

* Supra has teamed up with Maven to bring you something special – courses that our own community members have personally curated. And because you’re part of the Supra family, you can get up to 35% in some of these handpicked selections with code SUPRAxMAVEN.

* Check out Ben’s AI Practice Copilot and top-rated Maven course: Self-Paced PM Interview Bootcamp: Product Sense & Analytical Thinking (selected by Lenny Rachitsky as a top course 🔥). Get 25% off the course with promo code suprainsider (auto-applied here).

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit suprainsider.substack.com