Here's the power of startups: Posterous.com and loopt.com, both unknown to vast majority of people, had a short life, made no material impact and no one you know uses them now. However, the founders of even these startups went on to be famous power brokers on the back of the winds of these mostly failed startups.
An alternative view could be: YC selects their CEOs from very weak startups who managed to get amazing exists nonetheless.
An alt-alternative view: YC cannot select their CEO from successful startups because they are already successful and too busy being CEO of their own companies.
Having hung out with Thiel at Stanford, Tan must have had some idea about the nature of his true character. So how could he possibly have expected the experience of working under him to be any any way fun or positive?
As the AIDS crisis raged in the Bay Area, [Thiel's monthly opinion journal, The Stanford Review] printed treatises against “unnatural forms of sex” and “homophobia-phobia.” Chafkin writes that, when a Stanford senior was charged with sexual assault, the Review published an ardent defense of the rapist.
> Tan was Palantir's tenth employee, and his relationship with Thiel dates back to their college days at Stanford.
Wat? According to Wikipedia, Thiel was born in 1967, Tan in 1981. How could they have shared "college days at Stanford"?
More to the point of the article, "not meant to have a boss" is one of the cliche YC marketing lines, straight out of a pg essay. The only people who don't have a boss are people with FU money. Being a grinding startup founder doesn't mean you don't have a boss; it means you report to your board, and you have (maybe) a 0.1% chance of making FU money, instead of 0.000001% chance working as an employee.
> "I first met Peter at Stanford by inviting him to come speak at entrepreneurship events for the club I was president of, the Asia Pacific Entrepreneurship Society," Tan tells Insider.
Yeah. Some people just shouldn't hear this startup stuff. They'll bang their head against the wall for decades, driving themselves into desperation, and trying to pull the people around them into the spiral. It's like a relative who borrows to fund a gambling habit, except here they're desperately trying to feed an identity. Inside, incredible grandiosity and low self-esteem are superimposed.
An alternative view could be: YC selects their CEOs from very weak startups who managed to get amazing exists nonetheless.
An alt-alternative view: YC cannot select their CEO from successful startups because they are already successful and too busy being CEO of their own companies.