I'm actually middle management at a largish SV company, but I have also been leadership at smaller startups as well as the developer bootstrapping a 2-person SaaS app to 6-figure revenue, in addition to over a decade as a vanilla web developer working as an employee and freelancer.
What this experience has taught me is a visceral understanding of the leadership position (where you are responsible for the life and death of a company) and the IC position (where you are responsible for the nuts and bolts of shipping and operating internet-based software). In a small company it's easy to understand both sides. Once a company gets large the gulf is enormous.
I won't debate all your observations, other than to say that they are reductive and not reflective of the motivations and reasoning of executives I've known and worked with. To take one example:
> I'm always curious to understand why upper management folks are obsessed with keeping things chaotic
Chaos is not a goal (let alone obsession)— it is the merely the result of allowing significant individual agency among the creatives and craftspeople that do the work. The reason SV executives accept this is because reducing chaos requires a stronger command and control structure, but command and control structures don't work for building quality software products. Ultimately there are always minute details in the code and UX that end up being crucial and having outsized impact beyond where they are discovered. Most employees have your attitude of caring only about what is immediately asked of them by their supervisor ("I did what was expected, or more, and got rewarded for it, so doesn't really impact me"), but you actually need a healthy mix of people at the ground level who are intrinsically motivated by the overall quality of the product, and will work to resolve things with the global optimum in mind even if its "not their job". This is incredibly difficult work—often going unrecognized, or even posing a career risk, in some cultures—but absolutely necessary for any company that depends on customer satisfaction. The only way this can work is if the culture allows for good ideas to be floated from anywhere and acted on without being squashed by a rigid official-org-enforcing processes and bureaucracy.
What this experience has taught me is a visceral understanding of the leadership position (where you are responsible for the life and death of a company) and the IC position (where you are responsible for the nuts and bolts of shipping and operating internet-based software). In a small company it's easy to understand both sides. Once a company gets large the gulf is enormous.
I won't debate all your observations, other than to say that they are reductive and not reflective of the motivations and reasoning of executives I've known and worked with. To take one example:
> I'm always curious to understand why upper management folks are obsessed with keeping things chaotic
Chaos is not a goal (let alone obsession)— it is the merely the result of allowing significant individual agency among the creatives and craftspeople that do the work. The reason SV executives accept this is because reducing chaos requires a stronger command and control structure, but command and control structures don't work for building quality software products. Ultimately there are always minute details in the code and UX that end up being crucial and having outsized impact beyond where they are discovered. Most employees have your attitude of caring only about what is immediately asked of them by their supervisor ("I did what was expected, or more, and got rewarded for it, so doesn't really impact me"), but you actually need a healthy mix of people at the ground level who are intrinsically motivated by the overall quality of the product, and will work to resolve things with the global optimum in mind even if its "not their job". This is incredibly difficult work—often going unrecognized, or even posing a career risk, in some cultures—but absolutely necessary for any company that depends on customer satisfaction. The only way this can work is if the culture allows for good ideas to be floated from anywhere and acted on without being squashed by a rigid official-org-enforcing processes and bureaucracy.