Lessons from 6 software rewrite stories

A new take on the age-old question: Should you rewrite your application from scratch, or is that “the single worst strategic mistake that any software company can make”? Turns out there are more than two options for dealing with a mature codebase.

Herb Caudill
Feb 19, 2019 · 30 min read
Image for post
Image for post
Photo: Kevin Noble

Image for post
Image for post

1. Netscape

Image for post
Image for post
Key: 📝= rewrite, 💀 = dead end
Image for post
Image for post

Starting with a clean sheet

Image for post
Image for post
When the rewrite began, Netscape was losing ground quickly to Microsoft’s Internet Explorer. When the new browser was finally released three years later, it was buggy and slow; meanwhile Netscape’s market share had dwindled to practically nothing. (Chart adapted from Wikipedia.)

Lessons


Image for post
Image for post

2. Basecamp

Image for post
Image for post
Image for post
Image for post
Image for post
Image for post
37signals’ redesign of FedEx’s shipping form (left) is still better than the real thing, nearly two decades later.

Golden handcuffs

Image for post
Image for post

Sunset considered harmful

Image for post
Image for post
David compares Basecamp Classic to a Leica M3: It hasn’t been manufactured since 1967, but Leica is still committed to supporting it and repairing it for as long as they’re in business. (Photo Dnalor 01)
Image for post
Image for post

Lessons


Image for post
Image for post
Image for post
Image for post

3. Visual Studio & VS Code

Image for post
Image for post
Key: 😎 = hipster cred

Reaching out to the cool kids

Image for post
Image for post
VS Code has become the text editor of choice for JS hipsters. (Chart from State of JavaScript Survey, 2018)

Lessons

Image for post
Image for post
Of all the open source projects on GitHub, Visual Studio Code is ranked thirteenth by number of stars — coincidentally, just below Linux!

Image for post
Image for post

4. Gmail & Inbox

Image for post
Image for post
Key: 🌇 = sunset

Two interfaces, one service

Image for post
Image for post

Lessons


Image for post
Image for post

5. FogBugz & Trello

Image for post
Image for post
Key: 😟 = sad decline, 🤑 money money money

The strange story of Wasabi

An inflection point

A new hope

Image for post
Image for post
Image for post
Image for post

Meanwhile back at the ranch…

Lessons


Image for post
Image for post

6. FreshBooks & BillSpring

Image for post
Image for post
Key: 🕵️‍♀️ = undercover operation

Stop me if you’ve heard this before

What happened next may surprise you

Image for post
Image for post

Lessons


Some thoughts for now

Welcome to a place where words matter. On Medium, smart voices and original ideas take center stage - with no ads in sight. Watch

Follow all the topics you care about, and we’ll deliver the best stories for you to your homepage and inbox. Explore

Get unlimited access to the best stories on Medium — and support writers while you’re at it. Just $5/month. Upgrade

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store