But Shaikh had other ways of venting his frustration. He started a short-lived blog called YouSendItDeathwatch.com. He asked a lawyer about suing YouSendIt for wrongful termination and also considered taking YouSendIt to small-claims court, but he didn't pursue the cases. From time to time, mysterious changes would appear on YouSendIt's Wikipedia page. Sometimes Shaikh would be the only co-founder mentioned.
By the fall of 2008, Shaikh's projects were barely breaking even. FlyUpload had not panned out as he had hoped. Shaikh had ended up selling it for $50,000. Ucash.in had also failed to take off. "We are really dead," Shaikh wrote to Mahler in an e-mail. "Like dead dead dead...I'm not putting in more." Mahler wanted to keep going—and try to get back the $7,500 he had invested—but they ended up selling Ucash.in for a loss. By the end of 2008, the future of Perfect Acumen, the iPhone app company Shaikh had started with his wife, was still uncertain. Shaikh had sold his Porsche and was now driving a Mazda A3.
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." (Shaikh says he didn't write it.)
According to YouSendIt, the attack lasted for about 12 hours. Every time YouSendIt's engineering team found the source of the attack and blocked the IP address, Shaikh launched an attack from a new one. He managed to bring down the site for a total of four and a half hours. A week later, Kumaran reported the attacks to the FBI. He told them he suspected Shaikh.
Shaikh never imagined that authorities would be interested in his activities. To him, they amounted to nothing more than a prank, a way to blow off steam. Shaikh returned to work at his latest contract gig, at nVidia. He was unaware that federal agents were subpoenaing his Internet records—and quietly reaching out to his friends and associates.
As 2009 progressed, Shaikh began to find meaning apart from YouSendIt. His wife found out she was going to have a baby, due in September. And Perfect Acumen, the couple's iPhone app company, was finally getting off the ground. The developers in Pakistan were cranking out as many as five apps a day. Those apps may have generated upward of thousands of dollars a day in revenue before Apple eventually banned Perfect Acumen from its App Store for "persistent" infringement claims, according to a TechCrunch article in 2009. The tech blog argued that Apple's acceptance and subsequent rejection of more than 900 of Shaikh's hastily designed apps—including Top Sexy Ladies: Audrina Patridge, which sold for $4.99—revealed that "Apple doesn't know what the hell it's doing."
There were three more cyberattacks on YouSendIt in 2009. The last attack occurred just after midnight on June 14. About five hours later, changes to YouSendIt's Wikipedia page began appearing.
"Early 2005 [sic] Ranjith Kumaran hired Randy Korba, a Stanford GSB graduate in an attempt to take over the company while cutting communications with two founders Khalid Shaikh and Amir Shaikh," read the amended history. Another new addition capped things off: "Since then YouSendIt's traffic has dropped 10x..." (Shaikh won't confirm or deny responsibility for the attacks. He says he had nothing to do with the Wikipedia changes.)
On September 9, 2009, Shaikh got an alarming text from the teenage hacker he had partnered with: "Two guys at the door." The two guys turned out to be FBI agents who questioned the teen and seized his computer files—everything but his homework.
Shaikh didn't know what to make of it. The kid sometimes had mysterious ways of getting his hands on websites. Was it about that?
The following week, Shaikh got a call on his cell phone. It was Jan Mahler.
"A private investigator left me a voice mail," Mahler said. "What's going on? Why are they coming at me?" He said the investigator was asking about Perfect Acumen and YouSendIt—something about the servers being down.
Shaikh's wife, Saroash, who was due to give birth in two weeks and was at home watching TV, could hear the concern and confusion in her husband's voice. She suggested they all meet in person. Mahler offered to meet them at a Thai place in San Jose.
When the couple arrived, Mahler was already there, seated at a small table next to the wall. He spent the meal rehashing the previous events, looking for reasons someone might investigate. He mentioned he thought the FBI might be involved.
If Shaikh's and his wife's backs hadn't been to the window, they might have noticed a Chrysler in the parking lot with three men inside, watching them.
The next morning, after Shaikh went to work, his hugely pregnant and suspicious wife drove to the regional offices of the FBI and demanded to know what was going on. Agent Albert Fontana came out to meet her.
"Are you Khalid Shaikh's attorney?" he asked.
"No, I'm his wife!" she replied.
Fontana told her they wanted to speak with Shaikh and couldn't tell her anything unless he was there.
That night, the couple returned to the FBI office. Saroash was told to wait in the lobby while her husband was interviewed in an adjoining room. Because it was late on a Friday, and almost everyone at the FBI office had gone home, no one noticed when she got up and listened at the door. Inside, the agents asked Shaikh about his background. He told them about going to McGill, moving to the Valley, founding YouSendIt.
