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The Sordid Tale of Khalid Shaikh, the Founder-Turned-Attacker of File-Sharing Site YouSendIt

Everyone's worked for a terrible boss at one point or another that they would have loved to take down. It's rare when it actually happens, though. Rarer still is the case of a guy who destroys the company he founded after being given the boot. But that...
Khalid, left, at a Silicon Valley mixer in 2006. Via.

Everyone’s worked for a terrible boss at one point or another that they would have loved to take down. It’s rare when it actually happens, though. Rarer still is the case of a guy who destroys the company he founded after being given the boot. But that’s how Khalid Shaikh, co-founder of file sharing site YouSendIt, has found himself living in a Motel 6, awaiting sentencing for a cyberattack he used to destroy his former company’s servers.

Inc. has a great piece of reporting on Khalid’s history with YouSendIt, a Silicon Valley darling that he wrote the code and set up the servers for before serving as the firm’s first president. YouSendIt’s story is fascinating in that the three co-founders were clearly more savvy with tech than business, and through raising funding lost all control of their own company. Eventually, after a number of issues arose, Khalid was given the boot. From the piece.

In Shaikh’s absence, YouSendIt had continued to grow. It had raised an additional $14 million in VC funding and had 100,000 paying subscribers. Still, Shaikh marveled at how often YouSendIt’s site went down. He had even sent a tip about one of the outages to Valleywag, an industry gossip blog, which ignored his e-mail. If YouSendIt’s servers were still running the way he had left them, he believed, the site wouldn’t be crashing. At YouSendIt, Shaikh had been the subject of what he calls ‘senseless, mindless pressure’ to keep the servers running. Now, no one seemed to care. So, on a chilly Tuesday morning in December, Shaikh ran a piece of testing software, called ApacheBench, that flooded YouSendIt’s servers with traffic. The servers keeled over immediately. Later that day, a sentence appeared on YouSendIt’s Wikipedia page: ‘Looks like the company may be out of business, their site is down.’

Khalid’s story is a classic tale of revenge and intrigue, and the story’s worth the read for that alone. But it’s also an incredible glimpse into the boardrooms of the original Dot Com boom, in which guys with a ton of knowledge and good ideas were still ousted thanks to a lack of business acumen. And think, while Megaupload was shut down by the Feds, one of the earliest file-sharing sites was taken down by one of its own.

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