Essay · 25 min read

Rewrite, refactor, or reinvent? Lessons from 6 software rewrite stories

Herb Caudill · herbcaudill.com Free Intermediate

If you only read one piece on this question, make it this one. Caudill studies six real cases (Netscape, Basecamp, VS Code, Gmail, FogBugz to Trello, FreshBooks) and shows the choice is not just rewrite versus refactor. His recurring lesson is to build the new thing next to the old one rather than tearing down what already works and earns.

  • The real options are more than rewrite versus refactor
  • Successful rewrites kept the old product running the whole time
  • Build the new version alongside the old, do not replace it in one leap

The question it answers

  1. When is the right moment to stop iterating on the MVP and rebuild it properly, and how do I avoid the second-system rewrite trap?

Read with it

  1. The permission slip to recruit users by hand, do things manually, and deliver 'insanely great' experiences to your first few... paulgraham.com Essay · ~15 min read Do Things That Don't Scale Paul Graham
  2. Video · ~13 min How to Plan an MVP Michael Seibel (YC)
  3. The customer-development originator's clearest statement on scoping the minimum feature set to reach your earliest believers.... steveblank.com Article · ~8 min read Perfection by Subtraction, The Minimum Feature Set Steve Blank
  4. Long-form, candid interviews with Indian founders and investors on how they actually grew, distributed and built brand, one of... The Neon Show / Neon Fund Podcast · 200+ episodes The Neon Show (100x Entrepreneur Podcast) Siddhartha Ahluwalia
  5. Michael Seibel, who ran YC, makes the blunt case for shipping something almost embarrassingly simple and learning from real... Y Combinator Startup Library Video · ~10 min video How to Build an MVP Michael Seibel
  6. This is the canonical warning against throwing away working code and rebuilding from scratch, told through Netscape's rewrite... Joel on Software Essay · ~10 min read Things You Should Never Do, Part I Joel Spolsky
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