A Silicon Valley Tale of Humiliation and Revenge
He was fired from the company he helped create, YouSendIt. Then the cyberattacks started.
Vivienne Fleasher
Forced Out YouSendIt's first president, Khalid Shaikh
Courtesy Subject; Eva blue/Flickr; Courtesy Subject
The Old Crew YouSendIt's other co-founders, Amir Shaikh and Ranjith Kumaran, and former employee Jan Mahler.
Dillon O'Kelley
The New Normal The motel outside Denver where Khalid Shaikh now resides.
In Silicon Valley offices, the framed founder's doodle is as common as jewel-toned furniture and quirky conference-room names. But there's something peculiar about the drawing hanging in the colorful lobby at YouSendIt, an online file-sharing service based outside San Jose, California.
It started with a pen, a piece of paper, and an idea... reads bright blue type above two pages of ballpoint scribbles—sketches of the company's first homepage design, from 2003. Below the doodles is a vaguely inspirational quote: "Let's help our users start new kinds of conversations, ones they couldn't have before finding YouSendIt." —Ranjith Kumaran, Founder
Ranjith Kumaran didn't found YouSendIt on his own, though. Another man, one whom YouSendIt doesn't like to talk about, wrote the original code, built the first servers by hand, and served as the first president. His name is Khalid Shaikh, and he's 34. He was a computer-engineering student at McGill University and a former intern at Microsoft, and he once worked at Hewlett-Packard and Intel. More recently, he has been living in a Motel 6 outside Denver, awaiting sentencing for launching a cyberattack three years ago that crippled YouSendIt's servers.
The story of why—how a talented young entrepreneur turned on the company he worked so hard to help create—is at once bizarre and weirdly typical in the world of Silicon Valley tech start-ups.
"I've been involved with a hundred companies, and YouSendIt's development was very, very standard," says Nick Sturiale, a YouSendIt board member and partner at Jafco Ventures, a Palo Alto, California, venture capital firm. When he first met Shaikh, Sturiale says, "There was nothing he ever said, nothing he did that would ever indicate things to come."
Like so many entrepreneurs, Shaikh moved to Silicon Valley in 2000 with dreams of launching a tech company. Shaikh, who grew up in a blue-collar home in Montreal, the child of immigrants from Pakistan, fell in love with computers. At McGill, he had watched the dot-com boom from afar. He pictured Silicon Valley as being like The Gold Rush, a 1999 CNN documentary he loved, a place where Hotmail founder Sabeer Bhatia raced around in a Ferrari and venture capitalist Steve Jurvetson bet on start-ups as if he were working a roulette table.
Shaikh got a taste of the tech life during a Microsoft internship as a college sophomore. He took off as soon as he graduated: He married a conservative Muslim girl from Montreal (after getting permission from her father and his) and headed out to San Jose.
The boom was over when he arrived. Still, Shaikh had no trouble finding programming work. During his commutes, Shaikh marveled at how the Valley's leafy towns and office parks appeared like those of any other suburb—until a Ferrari would rip down the highway. He would excitedly follow the sports car in his Mitsubishi. When it inevitably pulled into a tech company's parking lot, his fantasies would rush back: Someday he would do that, too.
Shaikh was doing contract work for Symbol Technologies, a company that made bar-code scanners, when he befriended another dreamer, Jan Mahler. Like Shaikh, Mahler was in his 20s, grew up poor in a conservative religious family (Jehovah's Witnesses, in his case), and considered himself a proud geek. To amuse themselves at work, Shaikh and Mahler brought in chocolates for the staff every day—and secretly bet on whom they could make the fattest. After work, they would race down highway 85 in their Mitsubishis, hitting the off-ramp curves so hard, they screeched off exits.
Business would eventually complicate their friendship. In 2003, Shaikh told Mahler he planned to start a company. The business, later named YouSendIt, would let users send large files across the Web for free. Shaikh was having a conference call with his two co-founders to discuss it. Would Mahler like to join?
Mahler had met one of the other co-founders, Shaikh's older brother, Amir. The brothers were close; they had been apart only once, when Amir had worked in Chicago after getting his master's in computer engineering, also from McGill. Mahler had never met Ranjith Kumaran, the other co-founder, but he had heard about him from Khalid. Kumaran had been one of Khalid's programming partners at McGill. To the awkward and bearded Khalid, the trim and clean-cut Kumaran was smooth. Khalid raved about Kumaran's public-speaking skills.
Mahler declined to join the start-up. He couldn't imagine working with the brothers, who talked and bickered constantly. "They were annoying," he says. Besides, Mahler doubted their idea would work.
He was wrong. By the time YouSendIt debuted at the TiEcon tech conference in May 2004, the company had 300,000 users and was growing fast. The three co-founders split up the duties: Amir Shaikh sought advertising revenue, Kumaran focused on the user experience, and Khalid Shaikh handled the technical work. That turned out to be an increasingly mammoth task for Khalid, who was still working at his Symbol job. Traffic was increasing 30 percent a month, and the quantity of file downloads threatened to overwhelm the servers.
At night, working by hand on his living-room floor, Khalid built server after server. (He installed them in a nearby data center during his lunch breaks.) To save money, he used the smallest server cases available and drilled extra holes through the metal so he could cram in four hard drives. Sometimes, when he was drilling, the case would slip, and Khalid would cut himself, his blood mingling with the hardware.
Khalid's hard work earned him the title of president. In September 2004, when Cambrian Ventures made a $250,000 investment in YouSendIt, the co-founders' strategy was straightforward. "We didn't know what the hell we were doing when it came to funding," says Amir. "We just went ahead and bought more servers."
By the beginning of 2005, the co-founders had quit their day jobs and awarded themselves $120,000 salaries. That year, Khalid bought himself a Porsche Boxster, Kumaran bought a $650,000 house in San Jose, and Amir and his wife bought a five-bedroom house in New Jersey. (He would split his time between the two coasts.)
The company was on track to hit $1 million in revenue in 2005—enough to finance growth, but not enough to put YouSendIt on the fast track. The co-founders decided to get more funding.
