rewrite is an overarching daunting task. It's so much better to break rewrites into multiple steps. I went through several major rewrites with various startups

rewrite is an overarching daunting task. It's so much better to break rewrites into multiple steps. I went through several major rewrites with various startups so I think it works, but take it with grains of salt: 1. Throw away garbage first. Most companies including startups accumulate garbage code fairly quick. By just throwing away old ideas that didn't work, you have achieve a lot of gains already. There are many benefits doing this alone: tests run faster, compile time reduces, awk/grep became faster, etc. As startup founders/CTO, you can even held garbage throwing party once ever few months. Every programmer I know loves throwing away garbage code. 2. Ask stakeholders what are the primary use cases. Don't write a single line before doing this because it will be wrong, again. 3. When new technology is involved, perform load tests. Even the most trivial load tests would do. Doing this will inform you basic knowledge on how robust the tools are. 4. Rewrite 1 thing at a time and run tests in between so that your confidence stays high.