> The older I get, the more time I have to spend rebuilding reputation whenever I enter a new company.

This is very dependent on organizational structure. Some companies re-org so often that you’re still “proving your value” several years into your job, whereas other companies will recognize a first class developer on week one just by virtue of their work.

If you want to be at/near the top though, and really have an outsized impact, it’s best to start off there. You could be the CTO of a tiny company with big potential.