Crossword Perspectives with John Gruber
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Jul 10, 2025 
John Gruber, a renowned Apple journalist and the creator of Markdown, joins a deep discussion on the evolution of digital publishing. They explore the contrast between open and closed platforms, sharing insights on the impact of Markdown on writing. John reflects on WordPress's missed opportunities and its enduring appeal. The conversation also navigates the challenges independent creators face, the nostalgic evolution of Internet use, and the future of publishing in a subscription-based world.
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Substack Reveals WordPress Missed Chance
- Substack highlights a desire for readable, non-annoying media consumed via email instead of browsers.
- Its rise signaled a missed opportunity for WordPress to own this space and better serve independent media creators.
Use Platforms Then Graduate
- Start on easy-to-use platforms like Substack to begin publishing quickly.
- Plan to graduate to independent CMS solutions for technical independence and long-term control.
Open Web Shifted by Closed Apps
- The early web enabled anyone to publish openly with a simple URL and plain text content.
- Today, much media is consumed via closed proprietary apps, marking a shift from original web openness.