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Why did file sharing drive so much startup innovation?

One of the great things about editing all of our deep-dive EC-1 startup profiles is that you start to notice patterns across successful companies. While origin stories and trajectories can vary widely, the best companies seem to come from similar places and are conceived around very peculiar themes.
To wit, one common theme that came from our recent profiles of Expensify and NS1 is the centrality of file sharing (or, illegal file sharing if you are on that side of the fence) and internet infrastructure in the origin stories of the two companies. That’s peculiar, because the duo honestly couldn’t be more different. Expensify is an SF-founded (now Portland-based), decentralized startup focused on building expense reporting and analytics software for companies and CFOs. New York-based NS1 designs highly redundant DNS and internet traffic performance tools for web applications.
Yet, take a look at how the two companies were founded. Anna Heim on the origins of Expensify:
To truly understand Expensify, you first need to take a close look at a unique, short-lived, P2P file-sharing company called Red Swoosh, which was Travis Kalanick’s startup before he founded Uber. Framed by Kalanick as his “revenge business” after his previous P2P startup Scour was sued into oblivion for copyright infringement, Red Swoosh would be the precursor for Expensify’s future culture and ethos. In fact, many of Expensify’s initial team actually met at Red Swoosh, which was eventually acquired by Akamai Technologies in 2007 for $18.7 million.
[Expensify founder and CEO David] Barrett, a self-proclaimed alpha geek and lifelong software engineer, was actually Red Swoosh’s last engineering manager, hired after the failure of his first project, iGlance.com, a P2P push-to-talk program that couldn’t compete against Skype. “While I was licking my wounds from that experience, I was approached by Travis Kalanick who was running a startup called Red Swoosh,” he recalled in an interview.

How a band of P2P hackers planted the seeds of a unique expense management giant
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