Rewrites are almost always the wrong choice

Never do a rewrite, and there's good reasons for that... Trust me.

Engineers notoriously, notoriously, notoriously, massively underestimate the migration time for old system to new system and that causes a lot of problems.

If as a startup, whether it be early stage, but as a startup you focus too much on those marginal differences between groups of people, you can run the risk of making too many changes too soon and learning very little and adding crazy amounts of code complexity and overall organizational complexity to what you're building.