where he had children and no time at work to learn.

Using children as an excuse is laziness. It might not be as easy, but having children does not preclude you from learning new things or advancing yourself. It requires effort and planning, but frankly, using children as an excuse is wrong.

Keeping up with new tech requires time, and money.

It requires time and effort. Money is rarely an issue.

Even bigger "start ups" attempt to keep up the illusions of a smaller company

I'm going to assume that you just have bad experiences, because this is hardly my experience.