Much has been written about the many entrepreneurial successes that have come out of PayPal. After all, PayPal’s founders, executives, and employees have gone on to start such stalwarts as YouTube (the biggest hit of Web 2.0), LinkedIn (seemingly on its way to dominating the lucrative industry of business-oriented social networking), and Yelp (seemingly on its way to dominating local reviews…and hedonistic geek parties).

Much has also been written about the political views of Peter Thiel and the PayPal team. Even the New York Times has commented that many of PayPal’s top executives came from the conservative/libertarian student paper that Thiel co-founded while in college, The Stanford Review.

But what no one seems to have pointed out is the obvious fact that being a Silicon Valley Republican may very well be as strong a predictor of entrepreneurial success as being a Stanford CS grad student.

The reasons behind this surprisingly overlooked fact may be even more astonishing. A rock-ribbed belief in free enterprise can’t hurt, but I’m going to argue that the success of PayPal’s GOP mafia is simply the logical extension of one of the eternal truths of Silicon Valley: Outsiders make the best entrepreneurs.

And in our neck of the woods, Republicans are the ultimate outsiders.

In earlier eras, you could spot outsiders by their differences. In the 1970s, there were immigrants like Andy Grove. In the 1980s, there were retro-hippies like Steve Jobs and Sandy Lerner. They came from outside the establishment, which meant that they were willing to think different and disrupt the status quo.

Today, however, the so-called counterculture is the status quo, and a San Francisco mayor who earned national recognition as a gay marriage advocate is scorned locally as a tool of the business establishment.

When Peter Thiel and Dave Sacks were at Stanford, the political correctness movement was at its height, and the Democrats controlled the presidency and both houses of Congress. I recall one lecturer who refused to accept a paper from a student because it used the word “he” as the generic pronoun, rather than “she.” In that environment, Republicans were the renegades, and the Review boys (they were overwhelmingly male) rebelled against the Man by challenging the administration and battling the faculty members who tried to suppress their right to free expression.*

* It is important to note, in the interests of full disclosure, that according to some reports, some of the free speech rights that were exercised involved the use of derogatory terms for homosexuals.

It’s as if Hollywood made a sequel to Animal House, with the plucky, clean-cut Omegas rebelling against the heavy hand of a middle-aged Dean Blutarsky (who accepted the position after retiring from the Senate).

The lessons they learned in guerilla warfare served them well as PayPal fought off challenges from regulators, and direct competition from giants like eBay and Citibank, and in their other ventures, including their successful foray into Hollywood with Dave Sacks’ “Thank You For Smoking” (based on the satirical novel by Christopher Buckley, the son of conservative icon Willam F. Buckley).

So as you’re out searching for the next PayPal or YouTube, don’t ignore the earnest fellows with short haircuts. Consider attending a meeting of the Campus Republicans. The guy with the poster of Milton Friedman in his dorm room today may be tomorrow’s billionaire.

[You can read more of Chris Yeh’s prose on his ghetto old-school Blogger blog (up since 2001!), Adventures in Capitalism]

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