Has Claude’s Output Got Worse? Here’s What You Can Control | Re-release with Rob Webster
Early Adoptr: Simplifying AI For Founders & Small BusinessesShow Notes
Claude’s output has felt harder to work with recently. It ignores instructions, produces overlong, overwritten answers and can get worse over a long conversation. But if you want to improve your AI output, the answer might just be sitting in your Documents folder.
In this re-released episode, Jess and Kyle speak with Rob Webster, founder of TAU Marketing Solutions, about managing AI context. The tools and product names may be moving fast, but the practical problem has not changed: AI performs better when it has clear, well-managed context.
In this episode, Rob explains how to set up a few plain text files and folders so your AI knows who you are, what you do and what good looks like before you type a word. He also explains why giving your AI everything at once tends to make answers worse, how to spot when your setup has got bloated, and why the same files are the foundation for Claude Code and AI agents.
Follow Rob:
LinkedIn: https://www.linkedin.com/in/marketingaivisionary/ TAU Marketing Solutions: https://taums.ai/
What You'll Learn Why AI forgets instructions in long conversations, and how better context can improve output The difference between persistent and situational context How to organise plain-text and Markdown context files Why more connected documents do not always produce better AI answers What to retain permanently and what to remove when a project ends How to identify context drift early Why this approach provides a foundation for Claude Code, Claude Cowork and AI agents
Timestamps: 00:43 Introduction and Weekly Updates 03:09 Claude’s Output Has Got Worse, So We’re Revisiting Our Setups 11:12 Markdown Files and the Two Types of AI Context 14:24 Reintroducing Rob Webster 16:31 The Goldfish with a PhD: Why AI Forgets Everything 20:17 What You're Losing Every Time You Open Claude Without Context 26:11 Context Drift: Why AI Outputs Get Worse the More You Use It 29:26 How to Start Giving Your AI Context About Who You Are 35:35 Making It Stick: Naming Chats, Pinning Projects, Starting Your Folders 39:02 What a Working Folder Structure Actually Looks Like 40:38 Where Your Files Should Live 50:14 Global vs Project-Specific: The About Me Folder and Beyond 57:21 How AI Reads Context 59:47 How This Scales Into Agents, Claude Code, and Vibe Coding
Resources: https://tech-insider.org/anthropic-engineer-claude-writing-quality-worse-2026/ https://news.ycombinator.com/item?id=49348163 Get in touch with Early Adoptr: [email protected]
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