I feel he's the epitome of an armchair entrepreneur. He spouts a lot of advice on what not to do, how hard it is, how to beat the cold start problem, but never seems to get into the arena himself and show how successful implementing his principles could be.

(Yes, I'm aware he worked at Uber, but he never was responsible for turning it into a zero-awareness brand to a household brand. Not taking any credit away from that tho, and I actually agree with a lot of his content.)

I don't see Uber as a success. They used a big bag of cash to replace organised labour with cheaper, unorganised labour, much like how the mafia works but out in the open. It does not provide anything new, it's just cabs without licenses driven by people living in precarious conditions.

In some places they've been forced to ditch this business model too.

I try to explain to my kids that some expensive things and experiences are expensive because they need a "war chest" in case of lawsuit or recall. These companies have usually been in business a while.

Conversely, some things are cheap because the one who assumes all liability is oneself.