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Generally, you can't plan to be Larry Page, Sergey Brin, Mark Zuckerberg, Bill Gates, etc. Those are the guys who got it right the first time, but there are other models.

Elon Musk is a prominent example of how this alternative pattern works. He founded Zip2 (relatively unknown), then PayPal, then Tesla, and most recently SpaceX.

Evan Williams follows the same pattern. First PyraLabs (again, relatively unknown), then Blogger, then Twitter, now Medium.

In each case like the aforementioned two, you see a relatively small acquisition, followed by an explosion of ability and ambition.

This is the entire foundation of the "PayPal Mafia" - serial entrepreneurs who start out small (or relatively so) and then start serially disrupting greater markets.



Elon Musk is a good counterexample, yeah. That reminds me of one other ex-PayPal person: Russell Simmons founded Yelp after PayPal (though he wasn't a PayPal founder, just an early employee).

I mostly think of the PayPal Mafia as subsequently investors rather than founders, though. Spot-checking another 10 or so of the PayPal alumni, most seem to have gone the angel/VC route post-PayPal, rather than starting new businesses themselves.


> Mark Zuckerberg, Bill Gates, etc. Those are the guys who got it right the first time

See the sister comment for history on that. They are not known for their first startup




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