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Hey there,
A couple weeks ago, Herb Caudill wrote a long post outlining the lessons learned from 6 software rewrite stories to help answer the question, "Should we ever throw the whole thing out and rewrite it?"
Like most CTOs, I've wrestled with this question a couple times in my career. Almost no startups build the right product the first time around, and sometimes, MVPs (Minimum Viable Products) are so buggy as to become unusable at scale.
That said, rewrites have killed companies before, so starting from scratch is not always the right solution. Check out Herb's post and see the repercussions for Netscape, Basecamp, Visual Studio, GMail, FogBugz, and Fresh Books.
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Thanks for reading,

Karl Hughes, Portable CTO