AI for Solopreneur Systems: Two Projects That Actually Worked

AI for Solopreneur Systems: Two Projects That Actually Worked

From Streamlined Solopreneur: Automate Your Business, Take Time Off Worry-Free by Joe Casabona, Solopreneur Systems Coach

June 9, 2026 · 18 min · Season 2 · Episode 533

About this episode

Joe Casabona discusses two successful AI projects he created using Claude Cowork, including a custom Obsidian theme and a trip planning skill.

I talk a lot about the wrong ways to use AI. But a rainy weekend gave me a few free hours and two pet projects that I used Claude Cowork for— and the results actually impressed me. The first: I used Claude to vibe-code a custom Obsidian theme from scratch. No CSS, no digging through the inspector — just a few prompts and some back-and-forth until it looked exactly the way I wanted. The second: a Claude skill that plans trips for me end-to-end — packing list, budget, Todoist project, calendar entries, the works. It's now maybe my favorite thing I've ever built in Claude. Does all of this sound interesting, but you’re not sure where to start with your systems? Grab the free Solopreneur Systems Starter Kit — including the trip planning skill from this episode — at streamlined.fm/kit Links Handcrafted Obsidian Theme Obsidian Theme Screenshot Trip Template Screenshot (00:00) - Intro (01:28) - What AI is actually good at (and what it's not) (04:22) - Vibe-coding a custom Obsidian theme (11:00) - A Claude skill that plans trips end-to-end (17:42) - Wrap-up ———— Streamlined Solopreneur is the podcast for solopreneurs who want to automate their business and take time off worry-free. Each…

People in this episode

Host: Joe Casabona

Topics covered

  • AI
  • solopreneur systems
  • automation
  • trip planning
  • Obsidian theme

Keywords

  • AI
  • Claude Cowork
  • Obsidian theme
  • trip planning
  • automation
  • solopreneur

Mentioned in this episode

Products: Claude Cowork

Books & works: Obsidian, Todoist

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