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

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/

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Timestamps:

00:00 Introduction 03:48 Why Boring AI Habits Beat Impressive Ones 08:23 Two Kinds of Context: Always On vs Load When You Need It 10:50 Reintroducing Rob Webster 12:57 Why AI Forgets Everything Between Sessions 16:43 What You're Losing Every Time You Open Claude Without Context 22:37 Context Drift: Why AI Outputs Get Worse the More You Use It 25:52 How to Start Giving Your AI Context About Who You Are 32:01 Making It Stick: Naming Chats, Pinning Projects, Starting Your Folders 35:28 What a Working Folder Structure Actually Looks Like 37:04 Where to Store Your AI Context Files (Local vs Cloud) 46:40 Global vs Project-Specific: The About Me Folder and Beyond 53:47 How AI Reads Context 56:12 How This Scales Into Agents, Claude Code, and Vibe Coding

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