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Paid episode

The full episode is only available to paid subscribers of The AI Maker

Claude Skills Deep Dive: Why Your First Skill Will Break (And How to Fix It)

An hour long video walkthrough showing you how to build, debug, and deploy Claude Skills to automate your workflow.

I’m trying something new with this week’s post.

It’s a video walkthrough instead of my usual written guide.

Why? Because there’s too much nuance in building Claude Skills that I can’t capture in text alone. The edge cases, the files that break randomly, the weird formatting issues that only show up when you actually try to upload because I think you need to SEE this stuff to understand it.

In previous post, I showed you WHAT Claude Skills are and WHY they matter.

This week? HOW to actually build them without losing your mind.

Because here’s what nobody tells you: Claude generates messy files. Sometimes the skill.md is named wrong. Sometimes it references files that don’t exist. Sometimes it works perfectly in chat but breaks when you try to upload it.

I spent weeks figuring out these gotchas so you don’t have to. So I made you an hour-long video on how to do this.

Here’s what’s inside of the video

Part 1: Understanding the file structure

  • What’s actually inside a Claude Skill ZIP file

  • Why skill.md is the main instruction file

  • How Claude reads additional reference files for context

  • Real examples from my Strategic Decision Framework and Business Idea Generator Skill

Part 2: Building your first Skill

  • Live build: Editorial Assistant Skill from scratch

  • The exact moment when Claude generates broken files (and what to do)

  • How to identify when skill.md is incomplete or wrongly formatted

Part 3: Debugging with Claude Code

  • Setting up Claude Code in Cursor to analyze Skill files

  • Fixing missing reference files and broken instructions

  • Making Claude Code improve your Skill structure automatically

  • Why some Skills work perfectly and others need manual fixes

Throughout the video, I’m working with real examples:

  • Strategic Decision Framework (analyzes business decisions through 10 frameworks)

  • Business Idea Generator (transforms voice memos into validated concepts)

  • Editorial Assistant (the one we build live that breaks and we fix together)

But, this video got longer than I planned because we hit a real problem during the build.

Claude generated files with the wrong naming convention. The skill.md wasn’t in the right folder. Reference files were missing.

I kept it all in the video because that’s EXACTLY what you’ll experience when building your own Skills. I won’t hide the confusing cases in building Claude Skills. You can actually watch me debug when things inevitably break.

Before you watch the video, make sure you come prepared:

✓ Claude Pro account - $20/month

✓ Cursor or VS Code installed (for editing Skill files) - FREE

✓ Claude Code extension installed in your IDE - FREE

The video shows you every step: activating Skill Creator, building through chat, downloading files, fixing them in Claude Code, zipping correctly, and uploading to your account.

Download the Skills I reference:

All 7 Skills shown in the video are available on the Maker Access page:

  • Strategic Decision Framework

  • Business Idea Generator

  • Newsletter Repurpose to Social

  • SEO Content Optimizer

  • AI News Digest

  • Substack Notes Generator

  • Newsletter Brief Generator

Make sure you leveraged what I have provided.

P.S. Yes, the video shows me struggling with broken files for ~15 minutes around the 35-minute mark. I kept it in because that’s the real experience of building Skills. You’ll hit the same issues, and now you’ll know exactly how to fix them.

Until next week,

Wyndo

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P.P.S. If you get stuck building your first Skill, post the error inside Substack chat. I’ll help you debug. That’s what Maker Labs is for.

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