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Sorkin is where he is today, the most famous financial journalist of his generation, in large part because of his herculean work ethic. “He’s a tireless newshound,” Ingrassia told me. “I’ve seen few people in this business who work as hard.”

Sorkin grew up in Scarsdale, in the same milieu as that of his future Wall Street sources and readers. His father is a partner at the corporate-law firm Cahill Gordon and his mother is a playwright and librettist with a law degree. Before he fell for journalism, Sorkin loved business, especially the glamorous world of Madison Avenue. “I thought I wanted to be a copywriter,” Sorkin tells me. “As a kid, I used to watch the Super Bowl for the commercials.” He developed an entrepreneurial streak. At Scarsdale High School, Sorkin started a sports magazine and lured national advertisers like Champion and Wheaties to buy pages. He religiously read the Times’ advertising columnist, Stuart Elliott, to follow the ad business. In 1994, as a senior, he wrote Elliott a fan letter and asked to shadow him for five weeks. Officially, the Times didn’t have a high-school-internship program, but Sorkin persuaded them to let him in the door anyway. “They sort of were sneaking me in the building. I was the guy who would Xerox and staple things. I thought doing that was the coolest job in the world,” he says.

Sorkin impressed Glenn Kramon, then the Times’ deputy business editor, who allowed him to stay on at the paper through the summer. He wrote his first Times piece, a 400-word article on why dial-up modems make that ear-piercing screeching sound. At the Times, Sorkin schooled his elder colleagues in the new world of the web. “He helped several people start using their e-mail,” Elliott remembers.

When the summer ended, Sorkin left for Cornell, where he majored in communications. He continued to string for the Times and desperately hoped to land a full-time job at the paper. The Times didn’t have any openings but offered him contract work in the London bureau. It was the height of the dot-com boom, and London was a hive of deal-making. Sorkin started writing business stories for the Times. “In the beginning, I’d cold-call people,” he recalls. Sorkin found reporting easier in London than in New York. “It was the Wild West; it was a gossipy town,” he says. “I could leverage the expats who were there who wanted to show off back in New York. Every single Sunday, I worked the phones. I would not go to sleep unless I talked to 30 people in the day.”

Part of Sorkin’s problem at the ‘Times’ is that he’s a new sort of creature— entrepreneurial, web-friendly—at an essentially conservative institution.

After sixteen months in London, Sorkin was offered a job by a rival paper. The Times counteroffered with a full-time position back in New York. He was assigned to the paper’s mergers-and-acquisitions beat. He was 23. Immediately, Sorkin was covering major stories, including Chase’s acquisition of J. P. Morgan in a $30.9 billion deal.

When Sorkin arrived back in New York, the Times’ M&A coverage was sleepy. The bursting of the tech bubble had put an end to the furious wheeling and dealing of the nineties, and the Times, which had long trailed the Journal’s M&A coverage under the legendary reporter Steve Lipin, wasn’t a must-read in the deal-making world. Sorkin plunged into the beat. The universe of mergers and acquisitions is a tight constellation of some 200 elite bankers and lawyers. Sorkin, as he had done in London, set out to meet every one of these players. Sources at first didn’t take the Times seriously. “They made it clear that they left the Times at home with their wives and took The Wall Street Journal on the train in. That was an awakening to me,” Sorkin tells me.

Sorkin realized that to get sources, he needed to get his byline in front of the right people. In 2001, he came up with the idea for DealBook, an online newsletter he would e-mail to a list of Wall Street executives and other major players every morning with a roundup of all the major merger news of the day. “If I could get inside their e-mail box every morning, that would enhance our ability to break news,” Sorkin says. It would also enhance his brand.

It was a radical idea for the Times. The paper had never aggregated outside news under its flag before, and Sorkin had to convince his skeptical bosses that the paper could point its readers to competitors. He pitched DealBook to Martin Nisenholtz, who now oversees the Times’ digital operations. Brooks Brothers signed on as the inaugural sponsor. Initially, Sorkin anticipated an audience of 30,000 potential DealBook subscribers. Within a few months, they had attracted 80,000.


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