Confider #87: Malcolm Gladwell’s Crumbling Empire; Jezebel’s Downfall; and Geraldo’s CNN Dream

Welcome to this week’s edition of Confider, the media newsletter that pulls back the curtain to reveal what’s really going on inside the world’s most powerful navel-gazing industry. Subscribe here and send your questions, tips, and complaints here.

EXCLUSIVE — PUSHKIN IN PERIL: Forty years of friendship between media titans Malcolm Gladwell and Jacob Weisberg is being seriously tested as Pushkin Industries, the podcast company they co-founded together, navigates some extremely perilous cultural and financial headwinds, Confider has learned. Read the full Confider scoop here.

EXCLUSIVE — BEHIND THE FALL OF JEZEBEL: Months before G/O Media CEO Jim Spanfeller killed off Jezebel, management tasked staff with coming up with ad-friendly packages for the sales team to pitch to prospective sponsors, several former staffers told Confider. The request was handed down this past spring to Jezebel’s then-editor-in-chief Laura Bassett and called for employees—already stretched thin—to brainstorm on five ideas to make the site more “sellable” to ad buyers concerned about the site’s edgy content. After coming up with ideas, multiple sources said, the editorial staff was essentially ghosted, never receiving feedback from the sales team or management. In fact, interim editor-in-chief Lauren Tousignant told Confider she never met once with sales before last week’s shuttering. “It is not uncommon for editorial to come up with content packages for the ad sales team to take to the marketing community,” a G/O Media spokesperson said when reached for comment. A common task, indeed, but one that underscored hostilities between management and Jezebel, especially, as 404 Media first reported, the sales team eventually pressed Jezebel to nix the site’s “Sex. Celebrity. Politics. With Teeth” motto as a last-ditch effort to improve “brand safety.” G/O Media bosses also told Jezebel staff earlier this year to comply with company policy by removing curse words from headlines because it would negatively impact ad revenue, especially from programmatic ads. Additionally, Confider has learned that months before Axios reported that Lea Goldman, G/O Media’s deputy editorial director, led the company’s efforts to sell Jezebel, editorial director Merrill Brown—who was let go last week—proposed the idea of Bassett fundraising to purchase the site herself. After Bassett announced she’d left Jezebel in August, citing frustrations with Spanfeller and management, Brown suggested that she could use her Twitter clout to crowdfund the money to buy Jezebel. While Brown didn’t have the authority to offer the site to Bassett or a group of Jezebel alum, he did suggest they could buy the IP if they were able to raise $2 million, the amount needed to run the site for a full year. Defector, a site launched by ex-Deadspin staffers who quit en masse in 2019 after Spanfeller told them to “stick to sports,” first reported on Brown’s conversation with Bassett. Following Bassett’s exit, Jezebel staff was met with radio silence from management until they finally scored a meeting with Brown and Goldman last month, during which Goldman reassured them that Spanfeller had no plans to fold the famed site. At the same time, multiple sources told us, the pair were vague and non-committal about whether Jezebel was even being shopped around. After the Axios story came out several days after the meeting, rumors swirled within the Jezebel office about potential buyers. Several staffers told Confider that at one point they’d heard that Literally Media, owners of comedy website Cracked.com, sought a women’s brand and that Jezebel could fit that bill—a rumor Goldman denied when asked directly by Tousignant. “I would go so far to say that was maybe the only definitive answer I got on anything,” she told Confider.

Read more at The Daily Beast.