Thiel's "vast gates" have always been akin to the VIP door at the club - he wasn't born stinking rich, but he never had to sweat it. Sure - if you can afford to entrepreneurially start a company instead of working for one, do so. Keep in mind that the percentage of successful startups is smaller than the percentage of Google's non-advertising revenue.

This sort of interview dominates the tech industry like no other for two key reasons: (1) nobody looking for a programming job anticipates being there for long (2) nobody hiring for a tech job expects their employees to stick around long enough for their trainability to matter. The questions are what you know now and what you do when you don't. Things are different when you make specialized widgets with a specialized process and your employer expects to invest time in your position.

Nobody who is hiring fresh college grads is looking for someone they're gonna give a watch to in 25 years. They're looking for cannon fodder. Internal cannon fodder isn't even likely to be promoted faster than external cannon fodder so from the employer's perspective, there's nothing wrong with the process.