The PayPal Mafia

For those who might have lived under a rock for the past couple decades, PayPal is a genuine Silicon Valley legend. Launched during the dot-com bust by a team whose average age was just 23, PayPal amassed more than 25 million users in just over two years and was the first dot-com to successfully transition its user base to a paying status through use of the “Freemium” model. PayPal successfully drove giant competitors such as Western Union, AOL and Citibank out of its market and conducted the first successful post-bust technology pure-play IPO. In late 2002, PayPal ultimately merged with eBay for more than $1.5 billion (today it’s worth about $40 billion).

PayPal enabled an entrepreneurial revolution, helping to create literally millions of small businesses around the world, and provided a previously impossible level of monetary security for the masses by providing free offshore accounts denominated in the user’s choice of major currencies. But in addition to that, PayPal’s alumni have launched or provided early funding for more successful companies in a shorter time than the alumni of virtually any other company in history. Some of the more famous of these include YouTube, LinkedIn, Facebook, Yelp, Geni, Yammer, Rapleaf, Quantcast, CapLinked, Slide, Powerset, Palantir, Ironport, Xoom, Tesla Motors and SpaceX. As my friend Eric Jackson told Forbes back in 2006, the brain drain at PayPal was eBay’s loss, but the world’s gain.

It’s humbling to consider the accomplishments of my former colleagues, whom the media have dubbed the “PayPal Mafia.” I have had the honor to work alongside some of the most talented people ever assembled in Silicon Valley, as evidenced by the partial list below. These are just a few of their companies, and doesn’t begin to encompass the fullness of their influence.

UPDATE: Please read this outstanding story about us from Tech Republic. It may be the best article I’ve ever read on that time and what it birthed.

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Advanced Search Laboratories

Peter and Max might not have realized it at the time, but their company was more than just a successful dot-com. It turned out to be an entrepreneurial farm system. And today this new generation of innovative leaders has already transformed the business, technology and non-profit worlds. It’s only the beginning.


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Rod D. Martin is a technology entrepreneur, venture capitalist, hedge fund manager, author and conservative activist from Destin, Florida.