Season 1 · Episode 58 · June 24, 2026 · 1h 3m

Why Your AI Keeps Forgetting You, and the Folder That Fixes It (w/ Rob Webster)

Show Notes

AI has a memory problem. It is exceptionally capable within a session, helping you draft a pitch, review a contract, and write a client proposal in the same afternoon, but close the tab and it forgets everything. Open a new chat and you are back to square one, re-explaining who you are and what you do from scratch, every time, until it still never quite sounds like you.

This week, Rob Webster, founder of TAU Marketing Solutions, joins Jess and Kyle to explain why this happens and how a simple file and folder structure gives your AI permanent, reliable context, so you stop losing ground at the start of every session.

What You'll Learn

Why AI tools lose context between sessions
Why folder-based context is better than any system prompt
The difference between always-on context (the things permanently true about you, your role, and your business) and situational context you load in only for specific tasks or clients
How to build a simple folder structure , what files to put in it, and how tools like Claude read that context automatically so you don't have to paste it in every time
How to decide what information should live permanently in your files versus what's transitory context that should be removed once a project or idea is done
What "context drift" is and why long conversations degrade even when you've done the setup correctly — and how to catch it early
How this same folder structure becomes the foundation for more advanced AI work, including Claude Cowork and building your own AI agents

Rob Webster - https://www.linkedin.com/in/digitalstrategyleader/

TAU Marketing Solutions - https://taums.ai/

Use these links for a discount on the tools we recommend (and it supports the pod!)

Wispr Flow - AI-powered voice dictation that works across every app on your desktop - https://ref.wisprflow.ai/early-adoptr
Granola - The best AI meeting notes! New users get 100% off for their first month - https://www.granola.ai?via=early-adoptr