Lessons from 6 software rewrite stories (via) Herb Caudill takes on the classic idea that rewriting from scratch is “the single worst strategic mistake that any software company can make” and investigates it through the lens of six well-chosen examples: Netscape 6, Basecamp Classic/2/3, Visual Studio/VS Code, Gmail/Inbox, FogBugz/Wasabi/Trello, and finally FreshBooks/BillSpring. Each story has details I had never heard before, and the lessons and conclusions are deeply insightful.
Recent articles
- Highlights from my appearance on the Data Renegades podcast with CL Kao and Dori Wilson - 26th November 2025
- Claude Opus 4.5, and why evaluating new LLMs is increasingly difficult - 24th November 2025
- sqlite-utils 4.0a1 has several (minor) backwards incompatible changes - 24th November 2025