But what is the problem for those for who it doesn't work? How much do they get to lose? If they don't get accepted to the YC, they lose very little and it's just a short detour in their lives, certainly not the most boring or frustrating one, something to remember. If they get accepted to the YC, they clearly win vs the average folk because they get to know so many influential people and see how the world-class stuff gets done.
For example, i've been doing custom development for more than 20 years, made several million in the process, built over 130 project and i still don't have a slightest idea of how it's done - because every single of my client's projects failed - and i would be more than delighted to see how projects succeed first-hand even if the project wasn't mine.
I feel your example is a good portrayal of a life pretty much well-lived: you made money doing something you enjoy, met tons of people and fed your curiosity.
But according to this essay, you followed a BAD path not innovative enough, and the hidden reason why it's bad is because it will never generate any sort of profit for YC.
Now if you had tried 3 or 4 startups in that same timespan, burned through all your life savings, did not make several millions in the process, and failed all you endeavours, you will be applauded by YC.
Why ? because the more people exist like you, the better it is for them.
For example, i've been doing custom development for more than 20 years, made several million in the process, built over 130 project and i still don't have a slightest idea of how it's done - because every single of my client's projects failed - and i would be more than delighted to see how projects succeed first-hand even if the project wasn't mine.