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A lot of the time when they found the company I find the CEO knows a lot about it

Even if they were once the expert and know a lot about the area they just have too many other responsibilities to be the ground level expert and be ceo at the same time. A good ceo will delegate to folks that understand the details because details are the difference between success and failure.

That is the case with companies not started by the CEO. Flexport is a startup (YC, I think).

What do you mean by "ground level expert"? In my experience the true expertise tends to hover a couple of levels above 'ground level' and get called in for the curly questions. The actual boots-on-the-ground-100%-of-the-time people are usually at a fairly basic level of competence (or rapidly get promoted) and do the simple 'grunt work'.

I occasionally run into the higher levels these days and let me tell you, most of them are whip smart.

This is the kind of dumbass comment I see on HN that makes me roll my eyes. You sound like you're 3 years into your tech career and you can't help but comment on everything as if you're an expert but in reality you show your ignorance.