Digital disruption has felled many legacy media brands — independent local newspapers are on the endangered list and a flurry of print magazines, once fat with ads, have gone digital or shuttered entirely.
But the proliferation of social media and streaming services means there is more content than ever. It’s the gatekeepers who have changed, morphing from beetle-browed newspaper editors to journalist influencers who, in many cases, have fled or been pushed from legacy publications.
And the recent bloodbath at digital native brands including BuzzFeed and Vice has not quelled a growing crop of new media newsletter startups. With modest overhead — skeleton staffs, few brick-and-mortar offices and a paucity of health insurance plans — and seed money from venture firms or friends and family, they have set out to entice like-minded readers to pay for their work.
But in a crowded and fractured information landscape, churn equals death, or a severe devaluation at the very least. Will they survive? If they do, what will they look like in five or 10 years? Questions, questions.
Here, WWD Weekend looks at a few of the members of the new class of newsletters.
Air Mail
Graydon Carter’s Air Mail — aka “news for worldly cosmopolitans” — launched in 2019, two years after Carter’s 25-year stint atop the Vanity Fair masthead came to an end. He — and launch partner Alessandra Stanley, formerly of The New York Times — recruited stylish writers and editors and raised $15 million in series A funding at launch, with another $17 million in series B funding in 2021. The digital magazine is not yet profitable, but brings in about $15 million in revenue annually from a combination of subscriptions (readers pay $80 annually), advertising and commerce. Last March, Air Mail launched its first editorial spinoff, Air Mail Look, a stand-alone monthly title focused on beauty and edited by Linda Wells, which has its own tab on the Air Mail home page.
According to Carter, Air Mail has 300,000 subscribers, a figure that includes those who are on a one-month free trial, while a little more than 40 percent of revenue is derived from advertising, which is mostly from luxury brands such as Van Cleef & Arpels and Hermès. If Carter did not exactly reinvent a version of his old magazine, Air Mail nevertheless served to perpetuate his orbit amid New York’s cultural elite. He has plans for more editorial spinoffs, he has said, and is even exploring that most nostalgic of midcentury relics — a print magazine.
Puck
Puck, launched in 2021, built on the social media-driven, Substack-ification of journalism, recruiting what Jon Kelly, editor in chief and cofounder (with Max Theyan and Joe Purzycki, of The Athletic and Luminary, respectively), likes to describe as “generationally talented” writers who could build a following by delivering scoops. Kelly and his cofounders raised $7 million from James Coulter’s private equity firm TPG and Standard Investments in its initial round of funding. The writers — including Julia Ioffe, William D. Cohan, Matt Belloni and Dylan Byers — are incentivized to break news because they are essentially co-owners. For $100 annually, subscribers get access to the newsletters and podcasts. The $250 “Inner Circle” membership confers “off the record” calls with writers and “invites to exclusive in-person events,” but these plans are “limited.” Writers receive a base salary and $10,000 for every 1,000 subscribers they bring in above a certain threshold. (Puck has about 30,000 paid subscribers.)
Puck writers are very deliberately targeting the people they write about as readers, the monied CEOs about whose machinations Puck writers breathlessly chronicle with anonymous sourced revelations. As The New Yorker revealed, an advertiser pitch deck includes a pyramid of Puck’s audience. At the top of the pyramid are “Titans of Industry” followed by “Aspiring” and at the bottom, “Everybody Else.”
The Ankler
Started in 2017 by entertainment industry journalist Richard Rushfield as a one-man-band newsletter called The Ankler, former Hollywood Reporter editor Janice Min in 2021 engineered an expansion (and start-up cash) with a roster of additional newsletters, regular contributors (including Peter Kiefer, Vincent Boucher and Nicole LaPorte, Rushfield’s spouse) and podcasts. Ankler Media last year raised $1.5 million on a $20 million valuation, after completing Silicon Valley’s Y Combinator program. The company relies on digital advertising and subscriptions. The Ankler claims 49,000 subscribers, though it’s unclear how many of them are paying the $149 annual membership fee. The goal is to scale up as an indispensable read for/about the entertainment industry. And the WGA strike has given The Ankler an ongoing existential Hollywood crisis to chronicle as it builds readership. Imagine Entertainment Brian Grazer told Vanity Fair: “People in Hollywood like it. They think it’s titillating and find it largely truthful.”
Semafor Media
Hatched in 2022 by former BuzzFeed editor and New York Times media columnist Ben Smith and former Bloomberg Media CEO Justin Smith, Semafor is a free news site that covers global politics — and media — with short, often bulleted posts that studiously avoid partisan rancor. This makes it a little different from the rising tide of newsletters, which are very deliberately targeting a self-selecting readership willing to fork over cash for content. The company raised an initial $25 million before its launch in October 2022. But earlier this year it had to figure out how to buy out the $10 million infusion from its biggest investor, the alleged cryptocurrency fraudster Sam Bankman-Fried. The company generates revenue from digital advertising and sponsorship deals. And a deep roster of events has become a tenet of its business; there are about 40 planned for 2023, including a recent media summit in New York that featured former Biden administration press secretary and current MSNBC host Jen Psaki, ESPN’s Stephen A. Smith and CNN CEO Chris Licht. It was more successful than a now infamous pre-launch panel discussion cosponsored by the Knight Foundation centering on trust in the news, that included now-fired Fox News host Tucker Carlson. Semafor has a staff of about 60 people, including Ben Smith, whose media column runs with the slogan, “…we break the news behind the news.”
The Dispatch
Launched in 2020 by former Weekly Standard editor Stephen F. Hayes and former National Review editor Jonah Goldberg, The Dispatch offers “center-right” reporting for conservatives alienated by the slavish antics of the Trump wing of the Republican Party. The Dispatch was the first broader offering on Substack when it launched in January 2020, at the end of Donald Trump’s presidency and as a global pandemic was on the horizon. Hayes and cofounders Goldberg and Toby Stock raised about $6 million from individual investors in the runup to launch. The site has grown its staff and paying subscriber base to about 40,000; subscriptions are $100 annually or $1,500 for a lifetime membership. Last year, The Dispatch left Substack altogether. Hayes and Goldberg made headlines in 2021 when they both quit their gigs as paid contributors at Fox News in protest over Tucker Carlson’s “Patriot Purge” polemic, which falsely suggested that the January 2020 riot at the U.S. Capitol was a “false flag” attack engineered by the government as a pretext to persecute Trump supporters. (Hayes is now a contributor at NBC News). The Dispatch has since become a landing pad for other Fox News exiles: Chris Stirewalt, the veteran Fox News political editor, joined the title after his defenestration from the network for correctly calling Arizona for Joe Biden during the 2020 election.
The Free Press
A former opinion columnist at the New York Time, Bari Weiss launched her Substack newsletter Common Sense in 2021, a year after quitting the Times in a scathing and public resignation letter that accused her colleagues of bullying and harassment because her opinions ran counter to progressive orthodoxy. She quickly gained a large enough subscriber following on Substack to hire a small staff. Last December, Weiss and her wife, Nellie Bowles, essentially morphed Common Sense into The Free Press. The launch of the more robust site — there are 15 full-time staffers — coincided with The Twitter Files (archives of internal communications regarding the platform’s content moderation decisions given by Elon Musk to Weiss, Matt Taibbi and Michael Shellenberger). The Free Press mission statement may be a mouthful: “We publish investigative stories and provocative commentary about the world as it actually is — with the quality once expected from the legacy press, but the fearlessness of the new.” But Weiss has clearly found her fellow travelers. The Free Press has more than 330,000 subscribers, 50,000 of whom are paying, generating about $3 million annually, according to the Financial Times. Her recent Free Press podcast, “The Witch Trials of J.K. Rowling” (which includes an interview with the author) reached an audience of 5 million in its first two months.