Just a thought experiment: let's say we take Sam's ideas alongside something like UBI, where everyone has a baseline of income provided by the society they live in.
You succeed wildly, and get rich as an entrepreneur. Sadly, in a generation or two, your grandchildren will be back with the rest of the plebeians, despite grandpops launching YC, writing books on art and coding and creating an bunch of amazing companies. But, your grandkids are now not motivated by escaping the poverty they live in, but by a simple desire to live differently than the other normal people out there (also living on UBI).
This seems a lot like what happens in places like Russia or Venezuela or Brazil, where the best and the brightest (often from upper crust there) flee their countries to make it big in Europe, US or the Middle East, but not always because they have such horrible lives there.
Except that, unlike entrepreneurs driven by a mindset that has them feel like it is never enough, these ones are just trying to escape the ennui of boredom of suburbia, and slipping back into that isn't so awful. The alternative drive of escaping poverty does something very different and rapacious: see Tyco and Dennis Kozlowski: https://en.wikipedia.org/wiki/Dennis_Kozlowski, who despite enormous wealth couldn't stop himself from having his company pay for even his rugs.
It's like the best of communism, and the best of capitalism!
Seriously, isn't there an interesting space for entrepreneurs in a new world like the one Sam is describing?