Podcast Stefan Judis from Web Weekly on building a successful JavaScript newsletter, Career sustainability, AI, and Long term craft

DanielDecember 2, 2025

In this episode, I'm joined by Stefan Judis, the author of the Web Weekly newsletter (my favourite tech newsletter). I’d describe Stefan as a true web artisan, with a contagious enthusiasm for the craft of JS, CSS, and HTML.

We talked about how to run long-lasting projects, the process behind building his 6,000+ subscriber newsletter, learning deep vs. learning broad, AI and MCP, and many other topics. I had a blast recording this episode with Stefan, and I hope you’ll enjoy it just as much as I did. Let’s learn!

🔗 Links mentioned

• Stefan’s blog: https://stefanudis.com
• Web Weekly newsletter: https://webweekly.email
• Buttondown (newsletter platform): https://buttondown.email
• Raycast (AI & productivity launcher): https://www.raycast.com
• Interview with Stefan on Sachin K Mohan’s podcast: https://youtu.be/uHFDWqNX730

🎙️ Chapters & Topics

• 0:00 – 2:45 – Introduction, Stefan’s background
• 2:46 – 8:29 – Playing the long game: Passion, sustainability & how Stefan got into web development
• 8:30 – 11:09 – Podcasting and intrinsic motivation
• 11:10 – 16:28 – Behind the scenes of Web Weekly, reading habits, writing workflow
• 16:29 – 21:38 – Newsletter tech stack
• 21:39 – 23:33 – Monthly vs weekly publishing & the origin of “Web Weekly”
• 23:34 – 25:14 – Newsletter Sponsorships
• 25:15 – 30:27 – Deep vs shallow learning
• 30:28 – 33:16 – AI as a black box: Demystifying LLMs & engineering vs coding
• 33:17 – 36:27 – AI in writing: Grammarly replacement
• 36:28 – 41:42 – AI-generated content
• 41:43 – 44:49 – LLMs, Google Search
• 44:50 – 48:09 – Career growth through community, talks, blogging
• 48:10 – 51:20 – Burnout, health, sustainability
• 51:21 – 52:45 – Financial independence vs meaningful work
• 52:46 – 55:47 – Timeless web fundamentals: HTML, CSS, browser internals, performance
• 55:48 – 57:41 – MCP, AI agents, browser automation & what will last long-term
• 57:42 – 58:41 – One core principle to become a better developer: “Go deeper”
• 58:42 – 59:16 – Where to find Stefan online & closing thoughts