Answer extracted from the ACQ2 by Acquired podcast — listen to the full episode below.
Who was DealBook's first advertiser when it launched in 2001?
Brooks Brothers was the original advertiser for DealBook when Andrew Sorkin launched the newsletter in 2001. While the iconic menswear brand remains in business today, it has cycled through multiple closures and restructurings since then.
The early days of DealBook's advertising were remarkably lean by modern standards. Sorkin was building a new media business in the pre-Substack era, when few newsrooms had launched direct-to-reader newsletters or understood how to monetize digital content. Brooks Brothers stepping in as the first advertiser for the fledgling email newsletter says something about both the brand's marketing approach and the novelty of the medium at the time.
This detail is explored in the episode as part of Sorkin's broader origin story, revealing how DealBook evolved from a simple email into one of the most influential business news sources globally, ultimately reaching over one million subscribers across 25 years.
Andrew Sorkin — Anchor, CNBC Squawk Box; Founder, DealBook. Andrew Ross 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. The publication has grown to over one million subscribers and evolved into the New York Times' flagship business coverage platform. Beyond journalism, Sorkin is the co-creator of the HBO series Billions, author of two major books—Too Big to Fail and 1929—and host of the annual Dealbook Summit, held every December.
Discovering how Sorkin transformed a single advertiser relationship into a sustainable business model across multiple revenue streams is covered in depth in this episode, along with the broader context of how he built the Dealbook Summit into what hosts Ben Gilbert and David Rosenthal describe as "the flagship canonical business interview forum in the world."
From one advertiser to a media empire
Brooks Brothers' role as DealBook's first advertiser is more significant in retrospect than it might have seemed at launch. The brand was a natural fit for a newsletter aimed at investment bankers, hedge fund managers, and corporate executives—exactly the audience wearing Brooks Brothers suits. Yet the advertising relationship also reflects the scrappy realities of early digital media, when a single marquee advertiser could feel like a major victory.
The sustainability of DealBook came not from relying on one advertiser but from Sorkin's willingness to expand the format. The annual Dealbook Summit—launched to host in-person interviews with major business and political figures—became a marquee event that now attracts Fortune 500 leaders, government officials, and cultural figures. This diversification of revenue and reach transformed DealBook from a newsletter dependent on a handful of ad deals into an ecosystem spanning daily journalism, annual events, and multi-platform distribution.
See also
How did a reporter launch a daily email newsletter in 2001, over 15 years before Substack emerged?
Andrew Ross Sorkin started DealBook in 2001 after returning to New York from London, where he was covering mergers and acquisitions. He launched the newsletter as a daily email covering M&A deals and business news, building it from an initial addressable market of around 30,000 subscribers to over one million over 25 years.