Defining the chief of staff use case

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.

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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/

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