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Lessons from 6 software rewrite stories


Joel Spolsky once argued that rewriting from scratch is the single worst strategic mistake you can make.

Here’s an excellent article that investigates companies that have rewritten from scratch with success:

For many, Joel’s conclusion became an article of faith; I know it had a big effect on my thinking at the time.

In the following years, I read a few contrarian takes arguing that, under certain circumstances, it made a lot of sense to rewrite from scratch.

Read the article here. It is a fascinating read.


… They (Basecamp) made it easy for people to upgrade, but didn’t require them to leave Basecamp Classic. Not only that, but they’ve committed to continuing to host, support, and maintain Basecamp Classic indefinitely.

This is oh so inspiring, and the world is now truly a beautiful place, but three versions of Basecamp running in parallel require 3x on maintenance, security and support. Not everyone can afford that.

I look at this story as only a single data point and a survival bias manifestation. For one Basecamp which survived this model, there are probably hundreds who did not. If you are an idol in the project management field (as Basecamp is), your margins can cover the 3x expenses. But if you’re in a fierce competition with others, 3x expenses would just send you into the red.

Both products (VS Code and VS) are still actively developed

I don’t see why these two are considered a case of a rewrite. These are two separate products, with different markets.

Same for Trello vs. FogBugz - there was no rewrite. There was an abandonment of an existing product in favour of a new one that showed more potential. Even their use cases overlap only partially.

Freshbooks story was fun to read. Not cheap tho, too.