Malcolm Gladwell’s Media Empire Is Being Torn Apart

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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 the extremely perilous financial headwinds that have beset the industry, Confider has learned.

According to four people familiar with the situation, Gladwell has grown increasingly frustrated with how Weisberg has run their business, zeroing in on the serial lack of profitability at Pushkin. Staffers told us that the agreement between the co-founders was that Gladwell, a mega-star journalist and author, would attach his name to the company while Weisberg, the former top dog at Slate, would run the business.

Pushkin is home to wildly popular podcasts like Revisionist History, hosted by Gladwell; Against the Rules, hosted by fellow mega-star author Michael Lewis; and The Happiness Lab, hosted by Dr. Laurie Santos. But over the past year, the podcast industry has taken a severe hit, and Pushkin’s revenues have dwindled, resulting in layoffs to more than 30 percent of its staff in September.

Staffers who spoke with Confider pointed the finger at Weisberg’s handling of the business, with some lamenting how the media bigwig gave podcasts to his personal friends, such as Harvard Law professor Noah Feldman, while failing to aggressively pursue potentially more valuable podcasts from stars like Julia Louis-Dreyfus. Weisberg told Confider he made a “significant offer” to the Seinfeld star but she took her podcast elsewhere.

Concerns about the future of Pushkin Industries boiled over this summer, and in a July 12 all-staff meeting—audio of which was obtained and reviewed by Confider—Gladwell confessed to the limits of his involvement with the company and acknowledged his and Weisberg’s poor handling of it.

“We made mistakes. I think we grew too fast. I think we lost sight of who we are and what we stand for,” he admitted. “I think we got a little blinded by some of the hype and craziness in our industry over the last couple of years. I don’t think we took our financial crisis seriously enough back in January when we had the first round of layoffs and we regret all of that profoundly and sincerely.” (Pushkin’s financial backers include glamorous roofing company Standard Industries, Laurene Powell Jobs’ Emerson Collective, and Snap Inc. chair Michael Lynton.)

Elsewhere in the meeting, Gladwell conceded that his role is “vague,” that he lives full-time in the Hudson Valley, where Pushkin has a studio, and that he isn’t fully aware of the business side of things. “I’m a co-founder of this company. Jacob gave me the fancy title of president but I’m not an employee and I’m never going to be involved in the day-to-day decision making,” he said.

Gladwell further told staff that his priority is “making stuff,” noting that he recently pitched a Hollywood exec on an audiobook with Taylor Swift in the style of one Pushkin made with Paul Simon. Nevertheless, Gladwell pledged to staffers that he will be more present; and that he and Weisberg would be more honest and transparent about the company’s financial state.

Weisberg, meanwhile, told staff that he expected the company to achieve profitability in the second half of 2023 and that further layoffs weren’t expected. Two months later, however, the company announced a steep round of job cuts, plunging morale even lower.

“It’s been a tough year at Pushkin and for podcasting, but we’re friends for life, close collaborators, and fully aligned about the company,” Weisberg emailed Confider. “Malcolm’s role hasn’t changed. It extends not only to his own podcasts, including Revisionist History, but also to strategy and overall creative direction at Pushkin. We agreed to change his title to Editorial Director in September, when Gretta Cohn became President and I became Executive Chair.” Gladwell declined to comment.

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The question of what exactly Gladwell does at Pushkin Industries also came up during an AMA event that staffers did with the star figure.

“What Malcolm does is a lot. He does a lot for Pushkin. He’s working for Pushkin a lot,” Heather Fain, Pushkin’s COO and Gladwell’s former publicist, insisted to staffers during the event. “He is doing creative consulting on pods and the audiobooks side. He’s always coming up with new ideas for people to run through and chase down. He is really, really active in generating and securing advertising interest for our shows… Nobody works harder than he does. That guy is working all the time.”

The event took an especially uncomfortable turn, staffers told Confider, when Gladwell was asked for an update on the company’s diversity goals.

“My definition of diversity might be different from other people, but that’s part of diversity—allowing Malcolm to have a different definition of diversity than everyone else,” he said. When asked what diversity meant to him, Gladwell replied: “Here’s a question: If you’re a Republican, raise your hand.” When no one raised their hand, Gladwell remarked, “I would think that a diverse company should have some Republicans in it.”

When staffers pushed back, noting the lack of diversity among Pushkin’s senior leadership, Gladwell, who is half Black, responded, “Hello, I don’t count?”

Later on, when Gladwell was quizzed about whether Pushkin Industries could go up for sale, he told staffers that he would not be involved in any such discussions. “Even though it’s your company?” one employee asked in return. “It’s not my company,” Gladwell replied.

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