Tooling Tuesday: "Your AI-Ready Second Brain - Building in Obsidian with Claude" with Anne DeSpain

• ​From Notion to Obsidian: Why a traditional knowledge base hits its ceiling when you want AI to intelligently use what you know, and what the move to a local, AI-native system unlocks

• ​The agent interview: How Anne used Claude to interview herself, turning career history, client context, and domain knowledge into a structured knowledge base any AI can query in real time

• ​Auto-loading context: How every Claude session opens with the right knowledge already loaded, before a single word is typed, and why this single change improves every AI conversation that follows

• ​The save-to-vault skill: How meaningful work gets captured back into the knowledge base automatically, so the system compounds instead of staying static

​Anne DeSpain spent three decades as a retail executive at companies including Amazon, Sundance Catalog, and J. Crew. In early 2024, she founded DeSpain Consulting to help organizations put AI to work in practical, measurable ways.                                                                                           

Since making that pivot, Anne has built her own AI stack from the ground up, including a personal agent-ready knowledge base, automated marketing systems, agent-ready websites, and a multi-agent advisory council, all without a developer background. Her work sits at the intersection of deep operational experience and hands-on AI building, and she is focused on helping others do the same.

​Anne is based in Park City, Utah