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
- OpenAI are quietly adopting skills, now available in ChatGPT and Codex CLI - 12th December 2025
- GPT-5.2 - 11th December 2025
- Useful patterns for building HTML tools - 10th December 2025