Answer extracted from the ACQ2 by Acquired podcast — listen to the full episode below.
How did Andrew Ross Sorkin get his first assignment at the New York Times?
At 18 years old in 1995, Sorkin was arriving at the New York Times office with just a visitor pass, handling clerical work like xeroxing and stapling documents. An editor who had no idea how young he was overheard him discussing the Internet and spontaneously assigned him a story to write. His first published piece explained the noise that modems make, describing it as the "two modems talking to each other" over a phone line.
Sorkin had already shown signs of entrepreneurial ambition before joining the Times. He created Sports Page Magazine while in high school at Scarsdale High School in New York, which caught the attention of the newspaper. When he walked through the doors in 1995 at barely legal age, he wasn't assigned to a desk or given formal training—he simply started filling whatever small gaps needed filling.
The turning point came when an editor overheard a casual conversation about the Internet, which was still a novel topic at the time. Rather than dismiss the teenager as unqualified, the editor saw potential in his knowledge and handed him an assignment. Sorkin seized the opportunity, researching and writing about the technical sounds that modems produced—a topic few readers understood, but one perfectly suited to his natural ability to explain complex technology to a general audience.
This early piece about modem noise was entirely different from the financial journalism Sorkin would later become famous for. Yet it demonstrates how the ability to explain technical subjects clearly shaped his entire career. The assignment proved to be the gateway that transformed his visitor pass into a real position at one of the world's most prestigious newspapers.
Andrew Sorkin — Anchor at CNBC Squawk Box and Founder of DealBook. Sorkin joined the New York Times at age 18 in 1995 after creating Sports Page Magazine in high school in Scarsdale, New York. He founded DealBook in 2001 as an email newsletter covering mergers and acquisitions, growing it to over one million subscribers over 25 years. He is the co-creator of the television series Billions and author of two major books, Too Big to Fail and 1929, while hosting the annual Dealbook Summit.
What makes this story remarkable is how Sorkin's entry into journalism happened almost by accident. He wasn't hired through a formal process or brought in as an intern with clear expectations. Instead, an editor's moment of recognition—catching him in conversation about an emerging technology—created the opportunity. That same pattern of recognizing untapped potential in overlooked sources would later define his approach to investigative business reporting and his founding of DealBook, which revolutionized how financial news reached a mass audience years before the newsletter boom took hold.
See also
What was the initial market size expectation for DealBook compared to its actual growth?
When launching DealBook during the dot-com bust, the New York Times thought the total addressable market was 30,000 free subscribers. Today, DealBook has grown to over one million subscribers over 25 years.
What is the role of junior employees and 'jilted' insiders in uncovering major business stories?
Great stories often start at very junior levels, not just with senior people. Sorkin identifies what he calls the "jilted somebody"—someone who lost an argument, didn't get promoted, or was passed over—as a key source of major business stories.
How should journalists approach sources who have mixed or ulterior motives for sharing information?
Sorkin believes every source has some motivation for talking, and it is typically self-interested. Rather than worrying about their ultimate incentives, he confirms information from multiple sources or obtains documentation to verify the facts.