If someone loses 30 pounds of body fat and you ask them how they did it, would it be considered hacking the system if they told you that they worked out and ate healthy meals while restricting their caloric intake? To me, that's the expected normal way to go about losing weight and for the majority of people is guaranteed to work.
So it is possible to get extraordinary results through the application of discipline to boring, traditional approaches.
Regardless of whether it is or isn't "hacking the system", that answer tells you something about the someone in question. From that, I learn that they are able to exert focused discipline and flex willpower where others might not be able to.
I've flown a kite once in my life, as part of a competition, that I won. My kite flew more than twice as high as the next highest kite. After the competition, people asked how I got my kite so high, and my answer was just that I brought more string than they did. Some might attribute that to dumb luck, but I have a history of winning silly little competitions like this by being prepared.
I lost 40 pounds of body fat in 3 months by not eating carbohydrates, and eating an over 2000 calorie high fat diet. I think that losing 30 lbs of body fat the normal way isn't that extraordinary. I think what I did by hacking the system was more so extraordinary.
You've identified a task that 98% of motivated persons can accomplish. Building a billion dollar company is something that less than 2% of the YC companies have done.
Necessarily? Powerful incumbents can put up artificial barriers, but many times these players can be blindsided by the innovative competition anyway. So is America's economic system, and the full business environment for internet startups inherently caustic to new business ideas such that you have to work outside the system?
And are most YC applicants significantly revolutionary? How many systemic barriers would you expect to hit if you have some insight on how to build the next popular photo sharing app, for example? And if they are applying for YC and answering that question, it's not a safe assumption to make that the founders would have hit up against those barriers yet. A lot of YC founders are barely out of college and just turning their idea into reality.
It doesn't really matter how many of the applicants are revolutionary. But I can see that some of their biggest hits so far don't pay a lot of attention to following existing rules systems. And as pg has said numerous times now, it's the big hits that matter. The rest is noise.
Gmail was pretty revolutionary. Just out of curiosity... were the biggest obstacles more technology/product related or "human" (eg. making it an official Google product)?