Setups
Notion as the brain, Claude wired into Gmail, Drive, Calendar and Slack
Guy Yalif
Chief Evangelist at Webflow, which acquired Intellimize, the company he co-founded and ran as CEO, in 2024. Before that, VP Global Marketing at BrightRoll through its acquisition by Yahoo, and head of global product and industry marketing at Twitter through the IPO. Four exits, a Stanford MBA, and a handful of advisory seats.
Guy's second brain lives in Notion: the pages, the notes, every recorded call, and a personal CRM of companies and people. Claude reaches it and everything around it through connectors. What he built on top is the interesting part: a chief of staff, and a coach for one hard relationship.
How it fits together
BossGPT
A Custom GPT for one coworker. It reads your private DMs and emails with her, compares how she talks to you with how she talks to others inside and outside the company, and tells you how to communicate and frame things with her.
Chief of Staff
Three jobs, on top of the brain: plan my week, the goal of this day, and meeting prep.
From a conversation with Guy, 2026-08-27. To be reviewed by Guy before publishing.