Simon Willison’s Weblog

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.