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How about an entire company?

I worked for a dotcom back in the day. The underlying tech was appalling, to the extent they couldn't actually stay on the internet. We fixed this. They then proceeded to vastly expand the site, but every part of it was written as a special snowflake.

Five years later, they decided on a rebrand. This was literally a reskinning of the existing site. It took 50 odd people, ten months and more overtime than you care to think about. Many of those people were contractors.

Not only was this a huge expense, it prevented us from making the site any better. It was an extremely competitive market and the other sites ate our lunch. The next year was to be after round of redundancy, a financial statement that wrote the value of the business down to its cash reserves and finally a sell-off.

Ironically, the new owners turned it back into a viable business, but they had a very different attitude to technical debt.



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