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When I joined thredup.com as the very first employee and the 2nd programmer, we decided to do a complete rewrite. It ended up being a great decision.

I think that the real lesson to be learned is that you should beware of rules that start with "always" and "never".

And Joel didn't even hit on having financial independence. He didn't need to ship and didn't.

Agreed. You have all these great ideas on how to do things better, but along the way you inevitably forget all the work it took just to ship version 1 (let alone v2 with all this improvements both feature and design wise).