(in response to Quora question "Which strong beliefs on culture for entrepreneurialism did Peter / Max / David have at PayPal?")
Four aspects of early PayPal culture really stood out to me when I joined as a product manager:
1) self-sufficiency -- individuals and small teams were given fairly complex objectives and expected to figure out how to achieve them on their own. If you needed to integrate with an outside vendor, you picked up the phone yourself and called; you didn't wait for a BD person to become available. You did (the first version of) mockups and wireframes yourself; you didn't wait for a designer to become available. You wrote (the first draft of) site copy yourself; you didn't wait for a content writer.
2) extreme bias towards action -- early PayPal was simply a really *productive* workplace. This was partly driven by the culture of self-sufficiency. PayPal is and was, after all, a web service; and the company managed to ship prodigious amounts of relatively high-quality web software for a lot of years in a row early on. Yes, we had the usual politics between functional groups, but either individual heroes or small, high-trust teams more often than not found ways to deliver projects on-time.
3) data-driven decision making -- PayPal was filled with smart, opinionated people who were often at logger-heads. The way to win arguments was to bring data to bear. So you never started a sentence like this "I feel like it's a problem that our users can't do X", instead you'd do your homework first and then come to the table with "35% of our [insert some key metric here] are caused by the lack of X functionality..."
4) willingness to try -- even in a data-driven culture, you'll always run in to folks who either don't believe you have collected the right supporting data for a given decision or who just aren't comfortable when data contradicts their gut feeling. In many companies, those individuals would be the death of decision-making. At PayPal, I felt like you could almost always get someone to give it a *try* and then let performance data tell us whether to maintain the decision or rollback.
Those four cultural attributes actually make up a lot of the attitudes and beliefs that you'd expect to see in great entrepreneurs -- i.e., multi-disciplinary, self-sufficient, action-oriented, data-driven experimentalists. So it's no surprise to see the number of successful startup ventures founded by PayPal alums. To be sure, PayPal is/was not unique -- I would expect any company that established these kinds of cultural norms to produce a lot of entrepreneurs.
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